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研究生:羅玉婷
研究生(外文):Yu-Ting Luo
論文名稱:台灣石楠莖部及台灣馬錢根部之化學成分及生物活性之研究
論文名稱(外文):Studies on the Chemical Constituents and Biological Activities from the Stem of Pourthiaea lucida and the Root of Strychnos cathayensis
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:2007
畢業學年度:95
語文別:中文
論文頁數:187
中文關鍵詞:台灣石楠莖部及台灣馬錢根部之化學成分及生物活性之研究
外文關鍵詞:Strychnos cathayensisLoganiaceaestemDibenzofuranRosaceaePourthiaea lucidaindole alkaloidrootantitubercularH37Rvanti-inflammatory
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對台灣產植物-薔薇科台灣石楠莖部及馬錢科台灣馬錢根部,分別進行化學成分及生物活性之研究。
由台灣石楠莖材之乙酸乙酯可溶部,分離到一個具dibenzofuran骨架的新化合物:lucidafuran (1);及八個已知化合物,包括一個dibenzofuran:eriobofuran (2),二個biphenyls: aucuparin (3), 2’-methoxyaucuparin (4),五個steroids: stigmast-5-en-3β,7β-diol (5), β-sitosterol (6), stigmasterol (7), β-sitostenone (8)及stigmasta-4,22-dien-3-one (9)。
另外由台灣馬錢根部之乙酸乙酯可溶部分離到一個新的indole生物鹼:11,12-dimethoxyhenningsamine (10)及十七個已知化合物,包括兩個indole alkaloids: 12-hydroxy-11-methoxyhenningsamine (11), 11- methoxyhenningsamine (12),三個benzenoids: syringic acid (13), p- hydroxybenzoic acid (14), trans-p-coumaryl aldehyde (15),兩個coumarins: aesculetin dimethyl ether (16), 6,7,8-trimethoxycoumarin (17),一個2-quinolone: 4-methoxy-1-methyl-2-quinolone (18),一個α-tocopheranoid: α-tocopheryl quinone (19),兩個fatty acids: oleic acid (20), stearic acid (21),八個steroids: β-sitosterol (6), stigmasterol (7),βn 3β-hydroxystigmast-5-en-7-one (22), 3β-hydroxystigmasta-5,22-dien-7-one (23), 6β-hydroxy-stigmast-4-en-3-one (24)及6β-hydroxystigmasta-4,22-dien-3-one (25)。
上述分離化合物經由各種圖譜分析及文獻實驗數據比對一致而確認其結構。化合物1及 10為新化合物。化合物1及 3對fMLP誘導超陰氧離子的產生,具有良好的抑制活性,其IC50值分別為18.70 ± 4.40 及 17.04 ± 6.80 μΜ。此外,化合物 3亦具有良好的抗結核菌活性(MIC = 6.25 μg/mL, against Mycobacterium tuberculosis H37Rv)。
As a series of studies on the chemical constituents and biological activities of Formosan plants, the stem of Pourthiaea lucida (Rosaceae) and the root of Strychnos cathayensis (Loganiaceae) were investigated.
A new dibenzofuran, lucidafuran (1) and 8 known compounds were isolated and characterized from the stem of P. lucuda. The known compounds included a dibenzofuran, eriobofuran (2), two biphenyls, aucuparin (3), 2’-methoxyaucuparin (4), five steroids, stigmast-5-en-3β,7β-diol (5), β-sitosterol (6), stigmasterol (7), β-sitostenone (8) and stigmasta-4,22-dien-3-one (9).
In addition, investigation of an EtOAc-soluble fraction of the root of S. cathayensis has led to the isolation of a new indole alkaloid, 11,12-dimethoxyhenningsamine (10) and seventeen known compounds, including two indole alkaloids, 12-hydroxy-11-methoxyhenningsamine (11), 11-methoxyhenningsamine (12), three benzenoids, syringic acid (13), p-hydroxybenzoic acid (14), trans-p-coumaryl aldehyde (15), two coumarins, aesculetin dimethyl ether (16), 6,7,8-trimethoxycoumarin (17), a 2-quinolone, 4-methoxy-1-methyl-2-quinolone (18), a α-tocopheranoid, α-tocopheryl quinone (19), two fatty acids, oleic acid (20), stearic acid (21), eight steroids, β-sitosterol (6), stigmasterol (7), 3β-hydroxystigmast- 5-en-7-one (22), 3β-hydroxystigmasta-5,22-dien-7-one (23), 6β-hydroxy- stigmast-4-en-3-one (24), and 6β-hydroxy-stigmasta-4,22-dien-3-one (25).
The structures of the isolates were elucidated by spectral analyses and comparison of their physical and spectral data with literature. Compounds 1 and 10 are new compounds. Compounds 1 and 3 exhibited potent inhibition against fMLP-induced superoxide production with IC50 = 18.70 ± 4.40 and 17.04 ± 6.80μΜ, respectively. In addition, compound 3 exhibited marked antitubercular activity with MIC of 6.25μg/mL against Mycobacterium tuberculosis H37Rv.
目 錄
頁次
致謝......................................................I
目錄....................................................III
圖表目錄.......................................................VII
中文摘要 ..............................................XII
Abstract................................................XIV
第一章 緒言...............................................1
第二章 研究動機與目的.....................................4
第三章 過去成分研究概要
第一節 老葉兒樹屬與石楠屬植物過去化學成分研究概要.........6
第二節 馬錢屬過去化學成分研究概要........................20
第四章 抽出與分離
第一節 台灣石楠莖部之成分抽出與分離...............57
第二節 台灣馬錢根部之成分抽出與分離...............61
第五章 結果與討論
台灣石楠莖部
第一節 Lucidafuran (1)之結構研究......................66
第二節 Eriobofuran (2)之結構研究......................72
第三節 Aucuparin (3)之結構研究........................75
第四節 2’-Methoxyaucuparin (4)之結構研究.............78
第五節 Stigmast-5-en-3β,7β-diol (5)之結構研究.......81
第六節 混合物β-Sitosterol (6)與Stigmasterol (7)之結構研究...................................84
第七節 混合物β-Sitostenone (8)與Stigmasta-4,22-dien-3-one(9)之結構研究.........88
台灣馬錢根部
第八節 11,12-Dimethoxyhenningsamine (10)之結構研究.......92
第九節 12-Hydroxy-11-methoxyhenningsamine (11)之結構研究........97
第十節 11-Methoxyhenningsamin (12)之結構研究.........101
第十一節 Syringic acid (13)之結構研究................105
第十二節 p-Hydroxybenzoic acid (14)之結構研究........108
第十三節 trans-p-Coumaryl aldehyde (15)之結構研究....111
第十四節 Aesculetin dimethyl ether (16)之結構研究....114
第十五節 6,7,8-Trimethoxycoumarin (17)之結構研究.....117
第十六節 4-Methoxy-1-methyl-2-quinolone (18)之結構研究.....................120
第十七節 α-Tocopheryl quinone (19)之結構研究........123
第十八節 Oleic acid (20)之結構研究...................126
第十九節 Stearic acid (21)之結構研究.................129
第二十節 混合物3β-Hydroxystigmast-5-en-7-one (22)與3β-
Hydroxy stigmasta-5,22-dien-7-one (23)之結構研究.....................132
第二十一節 混合物6β-Hydroxystigmast-4-en-3-one (24)與
6β-Hydroxy stigmasta-4,22-dien-3-one (25)之結構研究................. 136
第六章 生物活性研究
第一節 抗發炎活性研究................................140
第二節 抗結核菌活性研究.................................141
第七章 結論.............................................142
第八章 實驗部份
第一節 儀器與材料....................................144
第二節 抽出與分離....................................146
2.1 台灣石楠莖部乙酸乙酯可溶部之分離....................147
2.2 台灣馬錢根部乙酸乙酯可溶部之分離....................149
第三節 抗發炎活性之實驗方法..........................152
第四節 抗結核菌活性之實驗方法........................154
第五節 各化合物之實驗數據............................156
第九章 參考文獻.........................................164
第十章 已發表之研究成果.................................187


圖 表 目 錄
圖A 台灣石楠之花枝..................................................3
圖B 台灣馬錢之果枝..................................................3
圖C 台灣石楠莖部之分離流程圖.................................... 57
圖D 台灣石楠莖部EtOAc可溶部之成分分離.......................58
圖E 台灣馬錢根部之分離流程圖.................................... 61
圖F 台灣馬錢根部EtOAc可溶部之成分分離...................... 62
圖1-1 Lucidafuran (1)之EI-MS圖譜.................................. 68
圖1-2 Lucidafuran (1)之IR圖譜...................................... 68
圖1-3 Lucidafuran (1)之1H-NMR圖譜................................ 69
圖1-4 Lucidafuran (1)之COSY圖譜.................................. 69
圖1-5 Lucidafuran (1)之NOESY圖譜................................ 70
圖1-6 Lucidafuran (1)之13C-NMR圖譜............................... 70
圖1-7 Lucidafuran (1)之HSQC圖譜.................................. 71
圖1-8 Lucidafuran (1)之HMBC圖譜................................. 71
圖2-1 Eriobofuran (2)之EI-MS圖譜.................................. 73
圖2-2 Eriobofuran (2)之IR圖譜....................................... 73
圖2-3 Eriobofuran (2)之1H-NMR圖譜................................ 74
圖3-1 Aucuparin (3)之EI-MS圖譜.................................... 76
圖3-2 Aucuparin (3)之IR圖譜........................................ 76
圖3-3 Aucuparin (3)之1H-NMR圖譜................................. 77
圖4-1 2’-Methoxyaucuparin (4)之EI-MS圖譜....................... 79
圖4-2 2’-Methoxyaucuparin (4)之IR圖譜............................ 79
圖4-3 2’-Methoxyaucuparin (4)之1H-NMR圖譜..................... 80
圖5-1 Stigmast-5-en-3β,7β-diol (5)之EI-MS圖譜................... 82
圖5-2 Stigmast-5-en-3β,7β-diol (5)之IR圖譜........................ 82
圖5-3 Stigmast-5-en-3β,7β-diol (5)之1H-NMR圖譜.................. 83
圖6-1 混合物β-Sitosterol (6)與Stigmasterol (7)之EI-MS圖譜....... 86
圖6-2 混合物β-Sitosterol (6)與Stigmasterol (7)之IR圖譜........... 86
圖6-3 混合物β-Sitosterol (6)與Stigmasterol (7)之1H-NMR圖譜.... 87
圖7-1 混合物β-Sitostenone (8)與Stigmasta-4,22-dien-3-one (9)之EI-MS圖譜.................................................... 90
圖7-2 混合物β-Sitostenone (8)與Stigmasta-4,22-dien-3-
one (9)之IR圖譜.......................................... 90
圖7-3 混合物β-Sitostenone (8)與Stigmasta-4,22-dien-3-one (9)之1H-NMR圖譜.................................................. 91
圖8-1 11,12-Dimethoxyhenningsamine (10)之EI-MS圖譜............94
圖8-2 11,12-Dimethoxyhenningsamine (10)之IR圖譜................ 94
圖8-3 11,12-Dimethoxyhenningsamine (10)之1H-NMR圖譜......... 95
圖8-4 11,12-Dimethoxyhenningsamine (10)之COSY圖譜........... 9595
圖8-5 11,12-Dimethoxyhenningsamine (10)之NOESY圖譜.......... 96
圖9-1 12-Hydroxy-11-methoxyhenningsamine (11)之EI-MS圖譜....97
圖9-2 12-Hydroxy-11-methoxyhenningsamine (11)之IR圖譜.........97
圖9-3 12-Hydroxy-11-methoxyhenningsamine (11)之1H-NMR圖譜..98
圖10-1 11-Methoxyhenningsamin (12)之EI-MS圖譜............... 103
圖10-2 11-Methoxyhenningsamin (12)之IR圖譜.................... 103
圖10-3 11-Methoxyhenningsamin (12)之1H-NMR圖譜............. 104
圖11-1 Syringic acid (13)之EI-MS圖譜............................ 106
圖11-2 Syringic acid (13)之IR圖譜................................. 106
圖11-3 Syringic acid (13)之1H-NMR圖譜........................... 107
圖12-1 p-Hydroxybenzoic acid (14)之EI-MS圖譜.................. 109
圖12-2 p-Hydroxybenzoic acid (14)之IR圖譜....................... 109
圖12-3 p-Hydroxybenzoic acid (14)之1H-NMR圖譜............... 11 110
圖13-1 trans-p-Coumaryl aldehyde (15)之EI-MS圖譜............. 112
圖13-2 trans-p-Ccoumaryl aldehyde (15)之IR圖譜................. 112
圖13-3 trans-p-Coumaryl aldehyde (15)之1H-NMR圖譜........... 113
圖14-1 Aesculetin dimethyl ether (16)之EI-MS圖譜............... 115
圖14-2 Aesculetin dimethyl ether (16)之IR圖譜.................... 115
圖14-3 Aesculetin dimethyl ether (16)之1H-NMR圖譜............. 116
圖15-1 6,7,8-Trimethoxycoumarin (17)之EI-MS圖譜.............. 118
圖15-2 6,7,8-Trimethoxycoumarin (17)之IR圖譜................... 118
圖15-3 6,7,8-Trimethoxycoumarin (17)之1H-NMR圖譜............ 119
圖16-1 4-Methoxy-1-methyl-2-quinolone (18)之EI-MS圖譜....... 121
圖16-2 4-Methoxy-1-methyl-2-quinolone (18)之IR圖譜........... 121
圖16-3 4-Methoxy-1-methyl-2-quinolone (18)之1H-NMR圖譜..... 122
圖17-1 α-Tocopheryl quinone (19)之EI-MS圖譜.................. 124
圖17-2 α-Tocopheryl quinone (19)之IR圖譜...................... 124
圖17-3 α-Tocopheryl quinone (19)之1H-NMR圖譜................. 125
圖18-1 Oleic acid (20)之EI-MS圖譜............................... 127
圖18-2 Oleic acid (20)之IR圖譜.................................... 127
圖18-3 Oleic acid (20)之1H-NMR圖譜............................. 128
圖19-1 Stearic acid (21)之EI-MS圖譜............................ 130
圖19-2 Stearic acid (21)之IR圖譜.................................. 130
圖19-3 Stearic acid (21)之1H-NMR圖譜........................... 131
圖20-1 混合物3β-Hydroxystigmast-5-en-7-one (22) 與3β-
Hydroxystigmasta-5,22-dien-7-one (23)之EI-MS圖譜..... 134
圖20-2 混合物3β-Hydroxystigmast-5-en-7-one (22)與3β-
Hydroxystigmasta-5,22-dien-7-one (23)之IR圖譜.......... 134
圖20-3 混合物3β-Hydroxystigmast-5-en-7-one (22) 與3β-
Hydroxystigmasta-5,22-dien-7-one (23)之1H-NMR圖譜... 135
圖21-1 混合物6β-Hydroxystigmast-4-en-3-one (24)與6β-
Hydroxystigmasta-4,22-dien-3-one (25)之EI-MS圖譜...... 138
圖21-2 混合物6β-Hydroxystigmast-4-en-3-one (24) 與6β-
Hydroxystigmasta-4,22-dien-3-one (25)之IR圖譜.......... 138
圖21-3 混合物6β-Hydroxystigmast-4-en-3-one (24)與6β-
Hydroxystigmasta-4,22-dien-3-one (25)之1H-NMR圖譜... 139
表1 老葉兒樹屬(Pourthiaea)植物過去分離的化學成分及文獻......6
表2 石楠屬(Photinia)植物過去分離的化學成分及文獻............ 12
表3 馬錢屬植物過去分離的化學成分及文獻 ....................... 30
表4 化合物之抗發炎活性...........................................140
表5 化合物之抗結核菌活性........................................ 141
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201.林碧芬,吳竹蘭,彭建芳,薛博仁,蔡文城,鄧麗珍,蘇維鈞。結核菌檢驗手冊,行政院衛生署疾病管制局,台北,2002























第十章 已發表之研究成果

一、國內研討會論文
1.Jih-Jung Chen*, Yu-Ting Lou, Tzu-Ann Wang, Ih-Sheng Chen, Sian-Rong Chen. A new dibenzofuran from Pouthiaea lucida. 2006台灣藥學會藥物化學研討會,大仁科技大學,2006, August 23-25.
2.Jih-Jung Chen*, Yu-Ting Lou, Chang-Hui Liao, Ih-Sheng Chen, Jia-Jen Tsai. New dibenzofuran and antiinflammatory constituents from the stem of Pourthiaea lucida. 2007台灣藥學會藥物化學研討
會,南投縣溪頭臺大實驗林,2007, May 18-20.
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