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研究生:卓瑞瑛
研究生(外文):Jui-ying Cho
論文名稱:山刈葉果實及狗花椒葉部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 Melicope semecarpifolia and the Leaves of Zanthoxylum avicennae
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:2008
畢業學年度:96
語文別:中文
論文頁數:266
中文關鍵詞:抗發炎山刈葉狗花椒
外文關鍵詞:Anti-inflammatoryZanthoxylum avicennaeMelicope semecarpifolia
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山刈葉為芸香科常綠的小喬木,分佈於台灣及菲律賓。而狗花椒為芸香科之常綠灌木,分佈於越南、菲律賓、中國南方及台灣。對台灣產植物進行抗發炎活性篩選,其中山刈葉果實與狗花椒葉部皆為活性植物。
由山刈葉果實之EtOAc可溶部,目前已分離出兩個新的benzoic acid derivatives: (E)-3-acetyl-6-(3,7-dimethylocta-2,6-dienyl-
oxy)-2,4-dihydroxylbenzoic acid (1)及(E)-3-acetyl-4-(3,7-dimethylocta-2,6-dienyloxy)-2,6-dihydroxybenzoic acid (2),三個新的acetophenones: (E)-1-(5-(3,7-dimethylocta-2,6-dienyloxy)-7-hydroxy-2,2-dimethyl-2H-chromen-8-yl)ethanone (3), (E)-1-(5-(3,7-dimethylocta-2,6-dienyloxy)-7-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-chromen-8-yl)ethanone (4)及(R,E)-1-(5-(3,7-dimethylocta-2,6-dienyloxy)-3,7-
dihydroxy-2,2-dimethylchroman-8-yl)ethanone (5),以及8個已知化合物。已知化合物中包括四個acetophenones: 2-(1’-geranyloxy)-4,6-dihydroxyacetophenone (6), 4-(1’-geranyloxy)-2,6-dihydroxyacetophenone (7), 2-(1’-geranyloxy)-4,6,β-trihydroxyacetophenone (8)及4-(1’-geranyloxy)-2,6,β-trihydroxyacetophenone (9),三個flavonoids: 5,4’-
dihydroxy-3,7,3’,4’-tetramethoxyflavone (10), 5,4’-dihydroxy-3,7,3’-trimethoxyflavone (11)及5,4’-dihydroxy-3,7-dimethoxyflavone (12),以及一個steroid: 3β-hydroxystigmast-5-en-7-one (13)。
另外自狗花椒葉部之EtOAc可溶部,分離出一個新的2-quinolone: 4-formyl-2-quinolone (14)及十一個已知化合物,包括三個benzo[c]-
phenanthridines: norchelerythrine (15), decarine (16), 6-acetonyldihydrochelerythrine (17),五個coumarins: aesculetin dimethyl ether (18), 6,7,8-trimethoxycoumarin (19), isoscopoletin (20), hydrangetin (21)及luvangetin (22),一個benzenoid: syringaldehyde (23),一個triterpenoid: squalene (24),以及一個steroid: β-sitosterol (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。
目前分離所得到的化合物中,2-(1’-geranyloxy)-4,6,β-trihydroxyacetophenone (8), 4-(1’-geranyloxy)-2,6,β-trihydroxyacetophenone (9), 5,4’-dihydroxy-3,7,3’,4’-tetramethoxyflavone (10), 5,4’-dihydroxy-3,7,3’-trimethoxyflavone (11)及5,4’-dihydroxy-3,7-dimethoxyflavone (12)對於formyl-L-methionyl-L-leuckyl-L-phenylalanine/cytochalasin B (FMLP/CB)誘導人類嗜中性白血球產生超氧陰離子(O2•–)及釋放彈性
蛋白酶(elastase)均具有良好的抑制活性 (IC50 < 4 g/mL)。
Melicope semecarpifolia (Merr.) T. G. Hartley (Rutaceae) is a small- to medium-sized evergreen tree found at lower altitude in forests of Taiwan and the Philippines. Zanthoxylum avicennae (Lam.) DC (Rutaceae) is an evergreen shrub distributed in Vietnam, Philippines, 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. Among them, M. semecarpifolia and Z. avicennae have been found to be active species.
In our search of compounds with anti-inflammatory activities, two new benzoic acid derivatives, (E)-3-acetyl-6-(3,7-dimethylocta-2,6-dienyloxy)-2,4-dihydroxylbenzoic acid (1) and (E)-3-acetyl-4-(3,7-dimethylocta-2,6-dienyloxy)-2,6-dihydroxybenzoic acid (2), three new acetophenones, (E)-1-(5-(3,7-dimethylocta-2,6-dienyloxy)-7-hydroxy-2,2-dimethyl-2H-chromen-8-yl)ethanone (3), (E)-1-(5-(3,7-dimethylocta-2,6-dienyloxy)-7-hydroxy-2-methyl-2-(4-methylpent-3-enyl)-2H-chromen-8-yl)ethanone (4), (R,E)-1-(5-(3,7-dimethylocta-2,6-dienyloxy)-3,7-dihydroxy-2,2-dimethylchroman-8-yl)ethanone (5) and 8 known compounds (9–13) have been isolated and identified from the fruits of M. semecarpifolia. Eight known compounds include four acetophenones, 2-(1’-geranyloxy)-4,6-dihydroxyacetophenone (6), 4-(1’-geranyloxy)-2,6-dihydroxyacetophenone (7), 2-(1’-geranyloxy)-4,6,β-trihydroxyacetophenone (8), and 4-(1’-geranyloxy)-2,6,β-trihydroxy-acetophenone (9), three flavonoids, 5,4’-dihydroxy-3,7,3’,4’-tetramethoxyflavone (10), 5,4’-dihydroxy-3,7,3’-trimethoxyflavone (11),
and 5,4’-dihydroxy-3,7-dimethoxyflavone (12), and a steroid, 3β-hydroxystigmast-5-en-7-one (13).
In addition, investigation of an EtOAc-soluble fraction of the leaves of Zanthoxylum avicennae has led to the isolation of a new 2-quinolone, 4-formyl-2-quinolone (14) and 11 known compounds (14–25), including three benzo[c]phenanthridines, norchelerythrine (15), decarine (16), and 6-acetonyldihydrochelerythrine (17), five coumarins, aesculetin dimethyl ether (18), 6,7,8-trimethoxycoumarin (19), isoscopoletin (20), hydrangetin (21), and luvangetin (22), a benzenoid, syringaldehyde (23), a triterpenoid, squalene (24), and a steroid, β-sitosterol (25).
The structures of above isolates were determined through spectral analyses and comparison of their physical and spectral data with
literature.
Among the isolated compounds, 2-(1’-geranyloxy)-4,6,β-
trihydroxyacetophenone (8), 4-(1’-geranyloxy)-2,6,β-trihydroxyacetophenone (9), 5,4’-dihydroxy-3,7,3’,4’-tetramethoxyflavone (10), 5,4’-dihydroxy-3,7,3’-trimethoxyflavone (11), and 5,4’-dihydroxy-3,7-
dimethoxyflavone (12) exhibited potent inhibition (IC50 < 4 g/mL) on superoxide anion generation and elastase release by human neutrophils in response to formyl-L-methionyl-L-leuckyl-L-phenylalanine/cytochalasin
B (FMLP/CB).
中文摘要............................................................................................................................................... 1
Abstract…………………....................................................................................................................... 3
第一章 緒言....................................................................................................................................... 6
第二章 研究動機與目的……………………………………………………………………….. 9
第三章 過去成分研究概要
第一節 三腳虌屬植物過去化學成分研究概要…………..……………………... 11
第二節 花椒屬植物過去化學成分研究概要……………………………………. 36
第四章抽出與分離
第一節 山刈葉果實之成分抽出與分離………………………………………… 106
第二節 狗花椒葉部之成分抽出與分離………………………………………… 112
山刈葉果實
第一節 (E)-3-Acetyl-6-(3,7-dimethylocta-2,6-dienyloxy)-2,4-dihydroxy-
benzoic acid (1)之結構研究……………………………………………… 118
第二節 (E)-3-Acetyl-4-(3,7-dimethylocta-2,6-dienyloxy)-2,6-dihydroxy-
benzoic acid (2)之結構研究…………………………….………………... 125
第三節 (E)-1-(5-(3,7-Dimethylocta-2,6-dienyloxy)-7-hydroxy-2,2-
dimethyl-2H-chromen-8-yl)ethanone (3)之結構研究…………….. 132
第四節 (E)-1-(5-(3,7-Dimethylocta-2,6-dienyloxy)-7-hydroxy-2-methyl-
2-(4-methylpent-3-enyl)-2H-chromen-8-yl)ethanone (4)之結構研究..…………………………………………………………………………….….. 139
第五節 (R,E)-1-(5-(3,7-Dimethylocta-2,6-dienyloxy)-3,7-dihydroxy-2,2-
dimethylchromen-8-yl)ethanone (5)之結構研究…………………… 146
第六節 2-(1’-Geranyloxy)-4,6-dihydroxyacetophenone (6)之結構研究..153
第七節 4-(1’-Geranyloxy)-2,6-dihydroxyacetophenone (7)之結構研究..156
第八節 2-(1’-Geranyloxy)-4,6,β-trihydroxyacetophenone (8)之結構研究....
……………………………………………………………………………………... 159
第九節 4-(1’-Geranyloxy)-2,6,β-trihydroxyacetophenone (9)之結構研究….
…………………………………………………………………………………….. 162
第十節 5,4’-Dihydroxy-3,7,3’,4’-tetramethoxyflavone (10)之結構研究.165
第十一節 5,4’-Dihydroxy-3,7,3’-trimethoxyflavone (11)之結構研究….. 168
第十二節 5,4’-Dihydroxy-3,7-dimethoxyflavone (12)之結構研究……… 171
第十三節 3β-Hydroxystigmast-5-en-7-one (13)之結構研究……………… 174
狗花椒葉部
第十四節 4-Formyl-2-quinolone (14)之結構研究……………………………. 177
第十五節 Norchelerythrine (15)之結構研究……………………………..……. 183
第十六節 Decarine (16)之結構研究……………………………………………… 186
第十七節 6-Acetonyldihydrochelerythrine (17)之結構研究………………. 189
第十八節 Aesculetin dimethyl ether (18)之結構研究……………………….. 192
第十九節 6,7,8-Trimethoxycoumarin (19)之結構研究……………………... 195
第二十節 Isoscopoletin (20)之結構研究………………………………………... 198
第二十一節 Hydrangetin (21)之結構研究……………………………………… 201
第二十二節 Luvangetin (22)之結構研究……………………………………….. 204
第二十三節 Syringaldehyde (23)之結構研究…………………………………. 207
第二十四節 Squalene (24)之結構研究………………………………………….. 210
第二十五節 β-Sitosterol (25)之結構研究………………………………………. 212
第六章 抗發炎活性研究………………….………………………………………………… 215
第七章 結論………………………………………………………………….…………………. 219
第八章 實驗部分
第一節 儀器與材料…………………………………….………………….…………... 221
第二節 山刈葉果實之抽出與分離…………………………………….………......223
第三節 狗花椒葉部之抽出與分離……………………………………….……......226
第四節 抗發炎活性測定……………………………………………………………... 228
第五節 化合物之實驗數據…………………………………………………….…..... 231
第九章 參考文獻…………………………………………….………………………………... 240
第十章 已發表之研究成果……………………………………………………………........ 265
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