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研究生:林文就
研究生(外文):Wen-Jiou Lin
論文名稱:樟芝子實體及台灣石楠葉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 BiologicalActivities from the Fruiting Bodies of Antrodia camphorataand the Leaves of Pourthiaea lucida
指導教授:陳日榮謝博銓
指導教授(外文):Jih-Jung ChenPo-Chuen Shieh
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:192
中文關鍵詞:子實體台灣石楠樟芝薔薇科葉部抗發炎抗結核菌多孔菌科
外文關鍵詞:fMLPPolyporaceaefruiting bodyRosaceaePourthiaea lucidaleaveMycobacterium tuberculosis H37RvAntrodia camphorata1 3-dioxolan-2-one derivativebenzenoidlong chain alkeneantitubercularanti-inflammatory
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樟芝(多孔菌科)是一種寄生在牛樟樹(樟科)腐朽心材內壁之多年生台灣特有真菌。樟芝在中國民俗療法中,曾被用來治療食物、酒精及藥物中毒、腹瀉、腹痛、高血壓、皮膚癢及肝癌等作用。對台灣產真菌進行抗發炎活性篩選,樟芝是其中一種具有活性的真菌。由樟芝子實體之正己烷可溶部進行成分分離,目前已分離出三個新的
benzenoids 化合物: antrocamphin A (1), antrocamphin B (2)及2,3,4,5-tetramethoxybenzoyl chloride (3)和一個新的1,3-dioxolan-2-one derivative: antrodioxolanone (4),以及13 個已知化合物: 4,7-dimethoxy-5-methyl-1,3-benzodioxole (5), 2,2’,5,5’-tetramethoxy-3,4,3’,4’-bimethylenedioxy-
6,6’-dimethylbiphenyl (6), (+)-sesamin (7), ?tocospiro
B (8), epi-friedelinol (9), antcin A (10), antcin B (11), dehydroeburicoic acid (12), ergosta-4,6,8(14),22-tetraen-3-one (13), eburicol (14), β-sitostenone (15), β-sitosterol (16)及stigmasterol (17)。
另外自台灣石楠(薔薇科)葉部之乙酸乙酯可溶部,分離出一個新的long chain alkene 化合物: 1-dotriacontene (24),以及12 個已知化合物: ?tocospiro B (8), β-sitostenone (15), β-sitosterol (16), ?tocospiro A (18), ?tocopheryl quinone (19), trans-phytol (20), 1-hexacosanol (21), 1-octacosanol (22), 1-triacontanol (23), methyl linoleate (25), 3β-hydroxystigmast-5-en-7-one (26)及friedelan-3-one (27)。
這些新化合物之結構經由各種圖譜分析,包括2D-NMR 實驗予以確認。將目前分離所得到的部份化合物進行抗發炎活性試驗,其中化合物1, 5, 10 及11 對於fMLP 所誘導超氧陰離子的產生(人類嗜中性白血球),呈現良好的抑制活性(IC50 ≤ 26.09 μM)。另外,在抗結核菌活性試驗中,化合物1 及20 呈現有效的抗結核菌(Mycobacterium tuberculosis H37Rv)活性,其MIC 值分別為6.25 及12.5 μg/mL。
Antrodia camphorata Wu, Ryvarden & Chang (Polyporaceae,
Aphyllophorales) is a parasitic fungus on the inner heartwood wall of the endemic species Cinnamomum kanehirai Hay. (Lauraceae) in Taiwan. It has been used for the treatment of food, alcohol and drug intoxication, diarrhoea, abdominal pain, hypertension, itching, and liver cancer in Chinese folk medicine. In a screening program searching for antiinflammatory compounds in Formosan fungi, A. camphorata was shown to be one of the active species. Investigation on the n-hexane-soluble
fraction of the fruiting body of A. camphorata has led to the isolation and characterization of three new benzenoids, antrocamphin A (1), antrocamphin B (2), and 2,3,4,5-tetramethoxybenzoyl chloride (3), and a new
1,3-dioxolan-2-one derivative, antrodioxolanone (4), together with thirteen known compounds and this included: 4,7-dimethoxy-5-methyl-1,3-benzodioxole (5), 2,2’,5,5’-tetramethoxy-3,4,3’,4’-bi-methylenedioxy-6,6’-dimethylbiphenyl (6), (+)-sesamin (7), ?tocospiro B (8),
epi-friedelinol (9), antcin A (10), antcin B (11), dehydroeburicoic acid (12), ergosta-4,6,8(14),22-tetraen-3-one (13), eburicol (14), β-sitostenone (15), and a mixture of β-sitosterol (16) and stigmasterol (17).
In addition, investigation on the EtOAc-soluble fraction of the leaves of Pourthiaea lucida has led to the isolation and characterization of a new long chain alkene, 1-dotriacontene (24), together with twelve known compounds and this included: ?tocospiro B (8), β-sitostenone (15), β-sitosterol (16), ?tocospiro A (18), ?tocopheryl quinone (19), transphytol (20), 1-hexacosanol (21), 1- octacosanol (22), 1-triacontanol (23), methyl linoleate (25), 3β-hydroxystigmast-5-en-7-one (26) and friedelan-3-one (27).
The structures of these new compounds were determined through spectral analyses including extensive 2D-NMR data. Among the isolates, 1, 5, 10 and 11 exhibited potent inhibition against fMLP-induced superoxide production (human neutrophils) with IC50 less than 26.09 μM. Compounds 1 and 20 also showed significant antitubercular activities in vitro (MIC = 6.25 and 12.5 μg/mL, respectively, against Mycobacterium tuberculosis H37Rv).
目 錄
頁次
中文摘要..................................................1
Abstract..................................................3
第一章 緒言........................................................5
第二章 研究動機與目的..................................13
第三章 過去成分研究概要
第一節 樟芝過去化學成分研究概要..........................15
第二節 老葉兒樹屬與石楠屬植物過去化學成分研究概要........34
第四章 抽出與分離
第一節 樟芝子實體成分之抽出與分離......................47
第二節 台灣石楠葉部成分之抽出與分離 ...................52
第五章 結果與討論
樟芝子實體
第一節 Antrocamphin A (1)之結構研究...................56
第二節 Antrocamphin B (2)之結構研究...................63
第三節 2,3,4,5-Tetramethoxybenzoyl chloride (3)之結構研
究....69
第四節 Antrodioxolanone (4)之結構研究.................75
第五節 4,7-Dimethoxy-5-methyl-1,3-benzodioxole (5)之結構
研究...........................................81
第六節 2,2’,5,5’-Tetramethoxy-3,4,3’,4’-bi-methylenedioxy-6,6’-dimethylbiphenyl (6)之結構研究......84
第七節 (+)-Sesamin (7)之結構研究......................87
第八節 α-Tocospiro B (8)之結構研究...................91
第九節 epi-Friedelinol (9)之結構研究..................95
第十節 Antcin A (10)之結構研究........................99
第十一節 Antcin B (11)之結構研究.....................103
第十二節 Dehydroeburicoic acid (12)之結構研究........107
第十三節 Ergosta-4,6,8(14),22-tetraen-3-one (13)之結構
研究........................................111
第十四節 Eburicol (14)之結構研究.....................115
第十五節 β-Sitostenone (15)之結構研究...............119
第十六節 混合物β-Sitosterol (16)與Stigmasterol (17)之結
構研究......................................122
台灣石楠葉部
第十七節 α-Tocospiro A (18)之結構研究...............126
第十八節 α-Tocopheryl quinone (19)之結構研究........130
第十九節 trans-Phytol (20)之結構研究.................133
第二十節 混合物1-Hexacosanol (21), 1-Octacosanol (22)與
1-Triacontanol (23)之結構研究...............136
第二十一節 1-Dotriacontene (24)之結構研究............139
第二十二節 Methyl linoleate (25)之結構研究...........144
第二十三節 3β-Hydroxystigmast-5-en-7-one (26)之結構研
究...147
第二十四節 Friedelan-3-one (27)之結構研究............151
第六章 生物活性之研究...................................154
第一節 抗發炎活性之研究...............................154
第二節 抗結核菌活性之研究.............................157
第七章 結論.............................................158
第八章 實驗部份
第一節 儀器與材料....................................160
第二節 樟芝子實體之抽出與分離........................162
第三節 台灣石楠葉部之抽出與分離......................166
第四節 抗發炎活性之實驗方法..........................169
第五節 抗結核菌活性之實驗方法........................171
第六節 化合物之實驗數據..............................173
第九章 參考文獻.........................................183
第十章 已發表之研究成果.................................192



圖 表 目 錄
頁次
圖A 樟芝(Antrodia camphorata Wu, Ryvarden & Chang) .............11
圖B 樟芝(Antrodia camphorata Wu, Ryvarden & Chang) .............11
圖C 台灣石楠(Pourthiaea lucida Decaisne)..........................12
圖D 台灣石楠(Pourthiaea lucida Decaisne) ..........................12
圖E 樟芝子實體之分離流程圖.......................................47
圖F 台灣石楠葉部之分離流程圖 ....................................52
圖1-1 Antrocamphin A (1)之EI-MS圖譜.............................. 58
圖1-2 Antrocamphin A (1)之IR圖譜 ..................................58
圖1-3 Antrocamphin A (1)之1H-NMR圖譜 ........................... 59
圖1-4 Antrocamphin A (1)之COSY圖譜 ............................. 59
圖1-5 Antrocamphin A (1)之NOESY圖譜 ...........................60
圖1-6 Antrocamphin A (1)之13C-NMR圖譜 ..........................60
圖1-7 Antrocamphin A (1)之DEPT圖譜 .............................61
圖1-8 Antrocamphin A (1)之HSQC圖譜 ............................61
圖1-9 Antrocamphin A (1)之HMBC圖譜 ...........................62
圖2-1 Antrocamphin B (2)之EI-MS圖譜 .............................65
圖2-2 Antrocamphin B (2)之IR圖譜 ................................. 65
圖2-3 Antrocamphin B (2)之1H-NMR圖譜 ........................... 66
圖2-4 Antrocamphin B (2)之NOESY圖譜 ...........................66
圖2-5 Antrocamphin B (2)之13C-NMR圖譜 ..........................67
圖2-6 Antrocamphin B (2)之HSQC圖譜 ............................ 67
圖2-7 Antrocamphin B (2)之HMBC圖譜 ........................... 68
圖3-1 2,3,4,5-Tetramethoxybenzoyl chloride (3)之EI-MS圖譜........71
圖3-2 2,3,4,5-Tetramethoxybenzoyl chloride (3)之IR圖譜 ............71
圖3-3 2,3,4,5-Tetramethoxybenzoyl chloride (3)之1H-NMR圖譜 ..... 72
圖3-4 2,3,4,5-Tetramethoxybenzoyl chloride (3)之NOESY圖譜 .....72
圖3-5 2,3,4,5-Tetramethoxybenzoyl chloride (3)之13C-NMR圖譜.....73
圖3-6 2,3,4,5-Tetramethoxybenzoyl chloride (3)之HSQC圖譜 ....... 73
圖3-7 2,3,4,5-Tetramethoxybenzoyl chloride (3)之HMBC圖譜 ...... 74
圖3-8 Methyl 2,3,4,5-tetramethoxybenzoate (3a)之1H-NMR圖譜 ... 74
圖4-1 Antrodioxolanone (4)之ESI-MS圖譜...........................77
圖4-2 Antrodioxolanone (4)之IR圖譜.................................77
圖4-3 Antrodioxolanone (4)之1H-NMR圖譜..........................78
圖4-4 Antrodioxolanone (4)之13C-NMR圖譜.........................78
圖4-5 Antrodioxolanone (4)之NOESY圖譜...........................79
圖4-6 Antrodioxolanone (4)之HSQC圖譜 ............................79
圖4-7 Antrodioxolanone (4)之HMBC圖譜............................80
圖5-1 4,7-Dimethoxy-5-methyl-1,3-benzodioxole (5)之EI-MS圖譜...82
圖5-2 4,7-Dimethoxy-5-methyl-1,3-benzodioxole (5)之IR圖譜....... 82
圖5-3 4,7-Dimethoxy-5-methyl-1,3-benzodioxole (5)之1H-NMR
圖譜............................................................. 83
圖6-1 2,2’,5,5’-Tetramethoxy-3,4,3’,4’-bi-methylenedioxy-6,6’-
dimethylbiphenyl (6)之EI-MS圖譜.............................85
圖6-2 2,2’,5,5’-Tetramethoxy-3,4,3’,4’-bi-methylenedioxy-6,6’-
dimethylbiphenyl (6)之IR圖譜................................. 85
圖6-3 2,2’,5,5’-Tetramethoxy-3,4,3’,4’-bi-methylenedioxy-6,6’-
dimethylbiphenyl (6)之1H-NMR圖譜..........................86
圖7-1 (+)-Sesamin (7)之ESI-MS圖譜.................................89
圖7-2 (+)-Sesamin (7)之IR圖譜.......................................89
圖7-3 (+)-Sesamin (7)之1H-NMR圖譜................................90
圖8-1 α-Tocospiro B (8)之EI-MS圖譜................................ 93
圖8-2 α-Tocospiro B (8)之IR圖譜....................................93
圖8-3 α-Tocospiro B (8)之1H-NMR圖譜............................. 94
圖9-1 epi-Friedelinol (9)之EI-MS圖譜................................97
圖9-2 epi-Friedelinol (9)之IR圖譜....................................97
圖9-3 epi-Friedelinol (9)之1H-NMR圖譜............................. 98
圖10-1 Antcin A (10)之EI-MS圖譜..................................101
圖10-2 Antcin A (10)之IR圖譜...................................... 101
圖10-3 Antcin A (10)之1H-NMR圖譜...............................102
圖11-1 Antcin B (11)之EI-MS圖譜..................................105
圖11-2 Antcin B (11)之IR圖譜......................................105
圖11-3 Antcin B (11)之1H-NMR圖譜 ............................... 106
圖12-1 Dehydroeburicoic acid (12)之EI-MS圖譜....................109
圖12-2 Dehydroeburicoic acid (12)之IR圖譜 ........................109
圖12-3 Dehydroeburicoic acid (12)之1H-NMR圖譜 .................110
圖13-1 Ergosta-4,6,8(14),22-tetraen-3-one (13)之EI-MS圖譜 .......113
圖13-2 Ergosta-4,6,8(14),22-tetraen-3-one (13)之IR圖譜............113
圖13-3 Ergosta-4,6,8(14),22-tetraen-3-one (13)之1H-NMR圖譜 .....114
圖14-1 Eburicol (14)之EI-MS圖譜..................................117
圖14-2 Eburicol (14)之IR圖譜.......................................117
圖14-3 Eburicol (14)之1H-NMR圖譜 ............................... 118
圖15-1 β-Sitostenone (15)之EI-MS圖譜.............................120
圖15-2 β-Sitostenone (15)之IR圖譜.................................120
圖15-3 β-Sitostenone (15)之1H-NMR圖譜 .........................121
圖16-1 β-Sitosterol (16)與Stigmasterol (17)之EI-MS圖譜..........124
圖16-2 β-Sitosterol (16)與Stigmasterol (17)之IR圖譜...............124
圖16-3 β-Sitosterol (16)與Stigmasterol (17)之1H-NMR圖譜........ 125
圖17-1 α-Tocospiro A (18)之EI-MS圖譜............................128
圖17-2 α-Tocospiro A (18)之IR圖譜................................128
圖17-3 α-Tocospiro A (18)之1H-NMR圖譜…......................... 129
圖18-1 α-Tocopheryl quinone (19)之EI-MS圖譜....................131
圖18-2 α-Tocopheryl quinone (19)之IR圖譜........................131
圖18-3 α-Tocopheryl quinone (19)之1H-NMR圖譜..................132
圖19-1 trans-Phytol (20)之EI-MS圖譜..............................134
圖19-2 trans-Phytol (20)之IR圖譜...................................134
圖19-3 trans-Phytol (20)之1H-NMR圖譜 ........................... 135
圖20-1 1-Hexacosanol (21), 1-Octacosanol (22)及1-Triacontanol (23)
之EI-MS圖譜................................................137
圖20-2 1-Hexacosanol (21), 1-Octacosanol (22)及1-Triacontanol (23)
之IR圖譜.....................................................137
圖20-3 1-Hexacosanol (21), 1-Octacosanol (22)及1-Triacontanol (23)
之1H-NMR圖譜.............................................. 138
圖21-1 1-Dotriacontene (24)之EI-MS圖譜 ..........................140
圖21-2 1-Dotriacontene (24)之IR圖譜 ...............................140
圖21-3 1-Dotriacontene (24)之1H-NMR圖譜 ........................ 141
圖21-4 1-Dotriacontene (24)之COSY圖譜...........................141
圖21-5 1-Dotriacontene (24)之NOESY圖譜 .........................142
圖21-6 1-Dotriacontene (24)之13C-NMR圖譜 .......................142
圖21-7 1-Dotriacontene (24)之HSQC圖譜...........................143
圖21-8 1-Dotriacontene (24)之HMBC圖譜 ..........................143
圖22-1 Methyl linoleate (25)之EI-MS圖譜 ..........................145
圖22-2 Methyl linoleate (25)之IR圖譜...............................145
圖22-3 Methyl linoleate (25)之1H-NMR圖譜........................ 146
圖23-1 3β-Hydroxystigmast-5-en-7-one (26)之EI-MS圖譜..........149
圖23-2 3β-Hydroxystigmast-5-en-7-one (26)之IR圖譜..............149
圖23-3 3β-Hydroxystigmast-5-en-7-one (26)之1H-NMR圖譜....... 150
圖24-1 Friedelan-3-one (27)之EI-MS圖譜...........................152
圖24-2 Friedelan-3-one (27)之IR圖譜...............................152
圖24-3 Friedelan-3-one (27)之1H-NMR圖譜........................ 153
表1 樟芝過去分離的化學成分及文獻............................... 20
表2 老葉兒樹屬植物過去分離的化學成分及文獻 .................. 34
表3 石楠屬植物過去分離的化學成分及文獻........................ 40
表4 化合物之抗發炎活性 ...........................................156
表5 化合物之抗結核菌活性 ........................................157
參考文獻

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