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研究生:蔡承軒
研究生(外文):Cheng-shuan Tsai
論文名稱:薑黃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 Curcuma longa
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:153
中文關鍵詞:抗發炎活性根莖薑黃薑科curculonone
外文關鍵詞:curculononeZingiberaceaeCurcuma longarhizomesanti-inflammatory activity
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薑黃為薑科之多年生草本植物,分佈遍及熱帶及亞熱帶地區,並廣泛的耕種於亞洲國家,且以印度與中國為主。對台灣產植物進行抗發炎活性篩選,其中薑黃為活性植物之一。
由薑黃乾燥根莖之CH2Cl2可溶部,目前已分離出六個新的sesquiterpenes,包括:curculonone A (1), curculonone B (2), curculonone C (3), curculonone D (4), 6α-hydroxycurcumanolide A (5)及1,10-de- hydro-10-deoxy-9-oxozedoarondiol (6),以及19個已知化合物 (7–25)。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,curculonone A (1), curculonone B (2), 6α-hydroxycurcumanolide A (5), zedoarondiol (12), curcumin (15), demethoxycurcumin (16)及1,5-bis(4-hydroxy-3-methoxylphenyl)-(1E, 4E)-1,4-pentadien-3-one (23)對於fMLP/CB所誘導超氧陰離子的產生,具有良好的抑制活性 (IC50 ≤ 18.22 μM)。此外,6α-hydroxy- curcumanolide A (5), zedoarondiol (12), demethoxycurcumin (16)及1,5-bis(4-hydroxy-3-methoxyphenyl)-(1E,4E)-1,4-pentadien-3-one (23)對於fMLP/CB所誘導彈性蛋白酶的釋放,亦具有良好的抑制活性 (IC50 ≤ 14.28 μM)。
關鍵詞:薑科、薑黃、根莖、抗發炎活性、curculonone
Curcuma longa L. (Zingiberaceae) is a perennial herb, distributed throughout tropical and subtropical regions of the world, being wildly cultivated in Asaitic countries, mainly in India and China. In our studies on the anti-inflammatory constituents of Formosan plants, many species have been screened for in vitro anti-inflammatory activity, and C. longa has been found to be one of the active species.
Bioassay-guided fractionation led to the isolation of six new sesquiterpenes, curculonone A (1), curculonone B (2), curculonone C (3), curculonone D (4), 6α-hydroxycurcumanolide A (5), and 1,10-dehydro- 10-deoxy-9-oxozedoarondiol (6), and 19 known compounds (7–25) from the rhizome of C. longa. The structures of all isolates were determined through spectral analyses and comparison of their physical and spectral data with literatures.
Among the isolates, curculonone A (1), curculonone B (2), 6α-hy- droxycurcumanolide A (5), zedoarondiol (12), curcumin (15), demetho- xycurcumin (16), and 1,5-bis(4-hydroxy-3-methoxylphenyl)-(1E,4E)- 1,4-penta-dien-3-one (23) exhibited inhibition (IC50 ≤ 18.22 μM) of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenyl-alanine/cytochalasin B (fMLP/ CB). In addition, 6α-hydroxycurcumanolide A (5), zedoarondiol (12), demethoxycurcumin (16), and 1,5-bis(4-hydroxy-3-methoxylphenyl)- (1E,4E)-1,4-pentadien-3-one (23) also inhibited fMLP/CB-induced elastase release with IC50 values ≤ 14.28 μM.
Key words:Zingiberaceae, Curcuma longa, rhizomes, anti-inflammatory activity, curculonone
目錄
頁次
第一章 緒言……………………………………………………………..1
第二章 研究動機與目的………………………………………………..2
第三章 過去化學成分研究概要…………………..……………………4
第五章 結果與討論……………………………………………………23
第一節 Curculonone A (1)之結構研究…………………….……. 23
第二節 Curculonone B (2)之結構研究………………………….. 31
第三節 Curculonone C (3)之結構研究………………………….. 38
第四節 Curculonone D (4)之結構研究………………………….. 45
第五節 6-Hydroxycurcumanolide A (5)之結構研究……….......52
第六節 1,10-Dehydro-10-deoxy-9-oxozedoarondiol (6) 之結構研究……………………………………………… 59
第七節 (S)-(+)-ar-Turmerone (7)之結構研究…………………… 66
第八節 Bisacurone (8)之結構研究………………………………. 69
第九節 Curlone (9)之結構研究………………………………….. 73
第十節 -Atlantone (10)之結構研究………………………….… 76
第十一節 (6R)-[(1R)-1,5-Dimethylhex-4-enyl]-3-methylcyclohex- 2-en-1-one (11)之結構研究…………………………... 79
第十二節 Zedoarondiol (12)之結構研究………………………... 82
第十三節 Curcumanolide A (13)之結構研究…………………… 85
第十四節 Curcumanolide B (14)之結構研究…………………… 88
第十五節 Curcumin (15)之結構研究……………………………. 91
第十六節 Demethoxycurcumin (16)之結構研究…………..……. 94
第十七節 Bisdemethoxycurcumin (17)之結構研究…………..….98
第十八節 Vanillin (18)之結構研究…………………………….. 101
第十九節 Vanillic Acid (19)之結構研究……………………….. 104
第二十節 (E)-Ferulic Acid (20)之結構研究………………….... 107
第二十一節 (Z)-Ferulic Acid (21)之結構研究…………………. 110
第二十二節 (E)-4-(4-Hydroxy-3-methoxyphenyl)but-3-en-2-one (22)之結構研究…………………………………… 113
第二十三節 1,5-Bis(4-hydroxy-3-methoxyphenyl)-(1E,4E)-1,4- pentadien-3-one (23)之結構研究…………….…… 116
第二十四節-Sitosterol (24)與Stigmasterol (25)之結構研究... 119
第六章 抗發炎活性研究…………………………………………….. 123
第七章 結論………………………………………………………….. 126
第八章 實驗部分…………………………………………….………. 128
第一節 儀器與材料……………………………………………. 128
第二節 薑黃根莖之抽取與分離……………………………….. 130
第三節 抗發炎活性之實驗方法……………………………….. 135
第四節 化合物之實驗數據…………………………………….. 138
第九章 參考文獻…………………………………………………….. 146
第十章 已發表之研究成果………………………………….............. 153




圖表目錄
頁次
圖C. 薑黃根莖部之分離流程圖............................................................14
圖D. 薑黃根莖部CH2Cl2層之成分分離...............................................15
圖1-1. Curculonone A (1)之ESI-MS圖譜..............................................26
圖1-2. Curculonone A (1)之HR-ESI-MS圖譜....................................... 26
圖1-3. Curculonone A (1)之IR圖譜....................................................... 27
圖1-4. Curculonone A (1)之1H-NMR圖譜(CDCl3, 400 MHz)..............27
圖1-5. Curculonone A (1)之HMBC圖譜................................................28
圖1-6. Curculonone A (1)之NOESY圖譜..............................................28
圖1-7. Curculonone A (1)之1H-1H COSY圖譜......................................29
圖1-8. Curculonone A (1)之HSQC圖譜.................................................29
圖1-9. Curculonone A (1)之DEPT圖譜..................................................30
圖1-10. Curculonone A (1)之13C-NMR圖譜(CDCl3, 100 MHz)...........30
圖2-1. Curculonone B (2)之ESI-MS圖譜..............................................33
圖2-2. Curculonone B (2)之HR-ESI-MS圖譜...……...……………….33
圖2-3. Curculonone B (2)之IR圖譜.......................................................34
圖2-4. Curculonone B (2)之1H-NMR圖譜(CDCl3, 400 MHz)..............34
圖2-5. Curculonone B (2)之NOESY圖譜..............................................35
圖2-6. Curculonone B (2)之1H-1H COSY圖譜......................................35
圖2-7. Curculonone B (2)之HSQC圖譜.................................................36
圖2-8. Curculonone B (2)之HMBC圖譜................................................36
圖2-9. Curculonone B (2)之DEPT圖譜.................................................37
圖2-10. Curculonone B (2)之13C-NMR圖譜(CDCl3, 100 MHz)...........37
圖3-1. Curculonone C (3)之EI-MS圖譜................................................40
圖3-2. Curculonone C (3)之HR-ESI-MS圖譜.......................................40
圖3-3. Curculonone C (3)之IR圖譜.......................................................41
圖3-4. Curculonone C (3)之1H-NMR圖譜(CDCl3, 400MHz)...............41
圖3-5. Curculonone C (3)之HMBC圖譜................................................42
圖3-6. Curculonone C (3)之NOESY圖譜..............................................42
圖3-7. Curculonone C (3)之1H-1H COSY圖譜......................................43
圖3-8. Curculonone C (3)之HSQC圖譜.................................................43
圖3-9. Curculonone C (3)之DEPT圖譜.................................................44
圖3-10. Curculonone C (3)之13C-NMR圖譜(CDCl3, 100 MHz)...........44
圖4-1. Curculonone D (4)之ESI-MS圖譜..............................................47
圖4-2. Curculonone D (4)之HR-ESI-MS圖譜........................................47
圖4-3. Curculonone D (4)之IR圖譜.......................................................48
圖4-4. Curculonone D (4)之1H-NMR圖譜(CDCl3, 400 MHz)..............48
圖4-5. Curculonone D (4)之HMBC圖譜...............................................49
圖4-6. Curculonone D (4)之NOESY圖譜..............................................49
圖4-7. Curculonone D (4)之1H-1H COSY圖譜......................................50
圖4-8. Curculonone D (4)之HSQC圖譜................................................50
圖4-9. Curculonone D (4)之DEPT圖譜................................................ 51
圖4-10. Curculonone D (4)之13C-NMR圖譜(CDCl3, 100 MHz)...........51
圖5-1. 6-Hydroxycurcumanolide A (5)之ESI-MS圖譜...................... 54
圖5-2. 6-Hydroxycurcumanolide A (5)之HR-ESI-MS圖譜................54
圖5-3. 6-Hydroxycurcumanolide A (5)之IR圖譜...............................55
圖5-4. 6-Hydroxycurcumanolide A (5)之1H-NMR圖譜(CDCl3, 400 MHz)............................................................................................ 55
圖5-5. 6-Hydroxycurcumanolide A (5)之HMBC圖譜........................56
圖5-6. 6-Hydroxycurcumanolide A (5)之NOESY圖譜.......................56
圖5-7. 6-Hydroxycurcumanolide A (5)之1H-1H COSY圖譜...............57
圖5-8. 6-Hydroxycurcumanolide A (5)之HSQC圖譜.........................57
圖5-9. 6-Hydroxycurcumanolide A (5)之DEPT圖譜..........................58
圖5-10. 6-Hydroxycurcumanolide A (5)之13C-NMR圖譜(CDCl3, 100 MHz).......................................................................................... 58
圖6-1. 1,10-Dehydro-10-deoxy-9-oxozedoarondiol (6)之ESI-MS圖譜 61
圖6-2. 1,10-Dehydro-10-deoxy-9-oxozedoarondiol (6)之HR-ESI-MS 圖譜..............................................................................................61
圖6-3. 1,10-Dehydro-10-deoxy-9-oxozedoarondiol (6)之IR圖譜.........62
圖6-4. 1,10-Dehydro-10-deoxy-9-oxozedoarondiol (6)之1H-NMR
圖譜(CDCl3, 400 MHz)............................................................... 62
圖6-5. 1,10-Dehydro-10-deoxy-9-oxozedoarondiol (6)之HMBC
圖譜……………………………………………………………..63
圖6-6. 1,10-Dehydro-10-deoxy-9-oxozedoarondiol (6)之NOESY
圖譜……………………………………………………………..63
圖6-7. 1,10-Dehydro-10-deoxy-9-oxozedoarondiol (6)之1H-1H COSY
圖譜............................................................................................. 64
圖6-8. 1,10-Dehydro-10-deoxy-9-oxozedoarondiol (6)之HSQC圖譜...64
圖6-9. 1,10-Dehydro-10-deoxy-9-oxozedoarondiol (6)之DEPT圖譜...65
圖6-10. 1,10-Dehydro-10-deoxy-9-oxozedoarondiol (6)之13C-NMR
圖譜(CDCl3, 100 MHz)............................................................. 65
圖7-1. (S)-(+)-ar-Turmerone (7)之ESI-MS圖譜....................................67
圖7-2. (S)-(+)-ar-Turmerone (7)之IR圖譜.............................................67
圖7-3. (S)-(+)-ar-Turmerone (7)之1H-NMR圖譜(CDCl3, 400 MHz)...68
圖8-1. Bisacurone (8)之ESI-MS圖譜.....................................................71
圖8-2. Bisacurone (8)之IR圖譜..............................................................71
圖8-3. Bisacurone (8)之1H-NMR圖譜(CDCl3, 400 MHz)....................72
圖9-1. Curlone (9)之ESI-MS圖譜..........................................................74
圖9-2. Curlone (9)之IR圖譜...................................................................74
圖9-3. Curlone (9)之1H-NMR圖譜(CDCl3, 400 MHz).........................75
圖10-1. -Atlantone (10)之ESI-MS圖...................................................77
圖10-2. -Atlantone (10)之IR譜............................................................77
圖10-3. -Atlantone (10)之1H-NMR圖譜 (CDCl3, 400 MHz)............. 78圖11-1. (6R)-[(1R)-1,5-Dimethylhex-4-enyl]-3-methylcyclohex-2-en-1-
one (11)之ESI-MS譜................................................................ 80
圖11-2. (6R)-[(1R)-1,5-Dimethylhex-4-enyl]-3-methylcyclohex-2-en-1-
one (11)之IR圖譜..................................................................... 80
圖11-3. (6R)-[(1R)-1,5-Dimethylhex-4-enyl]-3-methylcyclohex-2-en-1-
one (11)之1H-NMR圖譜 (CDCl3, 400 MHz).......................... 81
圖12-1. Zedoarondiol (12)之ESI-MS圖譜.............................................83
圖12-2. Zedoarondiol (12)之IR圖譜......................................................83
圖12-3. Zedoarondiol (12)之1H-NMR圖譜(CDCl3, 400 MHz).............84
圖13-1. Curcumanolide A (13)之ESI-MS圖譜......................................86
圖13-2. Curcumanolide A (13)之IR圖譜...............................................86
圖13-3. Curcumanolide A (13)之1H-NMR圖譜(CDCl3, 400 MHz)…..87
圖14-1. Curcumanolide B (14)之ESI-MS圖譜......................................89
圖14-2. Curcumanolide B (14)之IR圖譜...............................................89
圖14-3. Curcumanolide B (14)之1H-NMR圖譜(CDCl3, 400 MHz)…..90
圖15-1. Curcumin (15)之ESI-MS圖譜...................................................92
圖15-2. Curcumin (15)之IR圖譜............................................................92
圖15-3. Curcumin (15)之1H-NMR圖譜(CDCl3, 400 MHz)...................93
圖16-1. Demethoxycurcumin (16)之ESI-MS圖譜.................................96
圖16-2. Demethoxycurcumin (16)之IR圖譜..........................................96
圖16-3. Demethoxycurcumin (16)之1H-NMR圖譜(CDCl3, 400 MHz)...
................................................................................................... 97
圖17-1. Bisdemethoxycurcumin (17)之ESI-MS圖譜............................99
圖17-2. Bisdemethoxycurcumin (17)之IR圖譜.....................................99
圖17-3. Bisdemethoxycurcumin (17)之1H-NMR圖譜(CDCl3, 400 MHz)........................................................................................ 100
圖18-1. Vanillin (18)之ESI-MS圖譜...................................................102
圖18-2. Vanillin (18)之IR圖譜.............................................................102
圖18-3. Vanillin (18)之1H-NMR圖譜(CDCl3, 400 MHz)...................103
圖19-1. Vanillic acid (19)之ESI-MS圖譜............................................105
圖19-2. Vanillic acid (19)之IR圖譜......................................................105
圖19-3. Vanillic acid (19)之1H-NMR圖譜(CDCl3, 400 MHz).............106
圖20-1. (E)-Ferulic acid (20)之ESI-MS圖譜.......................................108
圖20-2. (E)-Ferulic acid (20)之IR圖譜................................................108
圖20-3. (E)-Ferulic acid (20)之1H-NMR圖譜(CDCl3, 400 MHz)…... 109
圖21-1. (Z)-Ferulic acid (21)之ESI-MS圖譜.......................................111
圖21-2. (Z)-Ferulic acid (21)之IR圖譜................................................. 111
圖21-3. (Z)-Ferulic acid (21)之1H-NMR圖譜(CDCl3, 400 MHz).......112
圖22-1. (E)-4-(4-Hydroxy-3-methoxyphenyl)but-3-en-2-one (22)之
ESI-MS圖譜...........................................................................114
圖22-2. (E)-4-(4-Hydroxy-3-methoxyphenyl)but-3-en-2-one (22)之IR圖譜..............................................................................................114
圖22-3. (E)-4-(4-Hydroxy-3-methoxyphenyl)but-3-en-2-one (22)之1H-NMR圖譜(CDCl3, 400 MHz)............................................115
圖23-1. 1,5-Bis(4-hydroxy-3-methoxyphenyl)-(1E,4E)-1,4-pentadien- 3-one (23)之ESI-MS圖譜.......................................................117
圖23-2. 1,5-Bis(4-hydroxy-3-methoxyphenyl)-(1E,4E)-1,4-pentadien- 3-one (23)之IR圖譜................................................................117
圖23-3. 1,5-Bis(4-hydroxy-3-methoxyphenyl)-(1E,4E)-1,4-pentadien- 3-one (23)之1H-NMR圖譜(CDCl3, 400 MHz).......................118
圖24-1. -Sitosterol (24)與Stigmasterol (25)之ESI-MS圖譜.............121
圖24-2. -Sitosterol (24)與Stigmasterol (25)之IR圖譜.......................121
圖24-3. -Sitosterol (24)與Stigmasterol (25)之1H-NMR圖譜(CDCl3, 400 MHz)................................................................................. 122
表1. 薑黃過去分離之化學成分及文獻.................................................. 6
表2. GC-MS偵測薑黃根莖之揮發油成分...........................................13
表3. 化合物之抗發炎活性................................................................... 125
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