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研究生: 郭宗孝
Kuo, Tsung-Hsiao
論文名稱: 過山香根部成分之研究
Studies on the root constituents of Clausena excavata
指導教授: 吳天賞
Wu, Tian-Shung
學位類別: 碩士
Master
系所名稱: 理學院 - 化學系碩士在職專班
Department of Chemistry (on the job class)
論文出版年: 2007
畢業學年度: 95
語文別: 中文
論文頁數: 132
中文關鍵詞: 過山香
外文關鍵詞: Clausena excavata
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  • 由過山香根部分離出50個化合物,經由光譜分析、化學方法及文獻比對後鑑定化合物的構造,分別為:3-methyl carbazole (2),murrayafoline A (5), clausine-P (6), girinimbine (8), carbazole-3-carbaldehyde (12), 3-formyl-1-hydroxycarbazole (15),murrayanine (16), 7-methoxy-9H-carbazole-3-carbaldehyde (17), clausine A (25), 7-methoxy-O- methylmukonal (28), 2-ydroxy-6,8-dimethoxy-9H-carbazole-3- carbaldehyde (30) , 2-hydroxy-1- (3-methyl-but-2-enyl)carbazole-3- carbaldehyde (37),clausine K (55), 2-hydroxy carbazole-3-carboxylic acid methyl ester (57), clausine E (58), mukonine (62), clausine C (63), clausine F (67), 8,8-dimiethyl-8H-pyrano[3,2-g]chromen-2-one (161), 5-methyoxy-8,8-dimethyl-8H-pyrano[3,2-g]chromen-2-one (163), 10- (1,1-dimethyl-allyl)-5-hydroxy-8,8-dimethyl-8H-pyrano-[3,2-g]chromen-2-one (166), hassanidin(168),kinocoumarin (169), 3,10-bis-(1,1-dimethyl allyl)-5-hydroxy-8,8-dimethyl-8H-pyrano[3,2-g]chromen-2-one (170), 10-(1,1-dimiethyl allyl)-5-hydroxy-8,8 dimethyl-7,8-dihydropyrano[3,2-g]chromene-2,6-dione (172), 1-O-methylcalusenolide (208), zapoterin (210), 3-methyl-carbazol-1-ol (240), 2-methyoxy carbazole-3-carbaldehyde (241), murrayacine (242), chrestifoline-A (243), clausenatine-A (244), N-(γ,γ-dimethylallyl)-1-methoxy-3-methylcarbazole (245), clausenanine-A (246*), clausenaine-B (247*), clausenanine-C (248*), clausebismine-A (249*), clausebismine-B (250*), clausebismine-C (251*), clausebismine-D (252*), clausetrimine-A (253*), clausecavine-A (254*), suberosin (255), marshdimerin (256), bisnorponcitrin (257), 5-O-acetylclausarin (258*), clausenabismarin-A (259*), methyl-p-bezenoate (260), δ-cuparenol (261), β-sitosterol&stigmasterol (262, 263);其中天然物首次發現之新化合物有3個:(250*), (253*), (258*);新化合物有7個:(246*), (247*), (248*), (249*), (251*), (252*), (259*);及新骨架之化合物1個:(254*)。

    A series of chromatographic separation has led to the isolation of fifty compounds from the acetone extract on the root of Clausena excavata. All compounds were characterized by comprehensive analyses of their 1D and 2D NMR and mass spectral data. They were named: 3-methyl carbazole (2), murrayafoline A (5), clausine-P (6), girinimbine (8), carbazole-3-carbaldehyde (12), 3-formyl-1-hydroxycarbazole (15), murrayanine (16), 7-methoxy-9H-carbazole-3-carbaldehyde (17), clausine A (25), 7-methoxy-O-methylmukonal (28), 2-hydroxy-6,8-dimethoxy-9H-carbazole-3-carbaldehyde (30) , 2-hydroxy-1-(3-methyl-but-2-enyl)carbazole-3-carbaldehyde (37), clausine K (55), 2-hydroxy carbazole-3-carboxylic acid methyl ester (57), clausine E (58), mukonine (62), clausine C (63), clausine F (67), 8,8-dimiethyl-8H-pyrano[3,2-g]chromen-2-one (161), 5-methyoxy-8,8-dimethyl-8H-pyrano[3,2-g]chromen-2-one (163), 10-(1,1-dimethyl-allyl)-5-hydroxy-8,8-dimethyl-8H-pyrano-[3,2-g]chromen-2-one (166), hassanidin (168), kinocoumarin (169), 3,10-bis-(1,1-dimethyl allyl)-5-hydroxy-8,8-dimethyl-8H-pyrano[3,2-g] chromen-2-one (170), 10-(1,1-dimiethyl allyl)-5-hydroxy-8,8 dimethyl-7,8-dihydropyrano[3,2-g]chromene-2,6-dione (172), 1-O-methylcalusenolide (208), zapoterin (210), 3-methyl-carbazol-1-ol (240), 2-methyoxy carbazole-3-carbaldehyde (241), murrayacine (242), chrestifoline-A (243), clausenatine-A (244), N-(γ,γ-dimethylallyl)-1-methoxy-3-methylcarbazole (245), clausenanine-A (246*), clausenaine-B (247*), clausenanine-C (248*), clausebismine-A (249*), clausebismine-B (250*), clausebismine-C (251*), clausebismine-D (252*), clausetrimine-A (253*), clausecavine-A (254*), suberosin (255), marshdimerin (256), bisnorponcitrin (257), 5-O-acetylclausarin (258*), clausenabismarin-A (259*), methyl-p-bezenoate (260), δ-cuparenol (261), β-sitosterol&stigmasterol (262, 263). Among these isolates, compounds (250*), (253*), (258*) were reported for the first time from natural sources. And seven compounds which named clausenanine-A (246*), clausenaine-B (247*), clausenanine-C (248*), clausebismine-A (249*), clausebismine-C (251*), clausebismine-D (252*), clausenabismarin-A (259*) are new compounds. A new compound with new skeleton was named clausecavine-A (254*).

    Abstract ..................... 1 中文摘要 ....................................... 2 第一章 緒論 ........... 3 第一節 研究動機 ......................... 3 第二節 植物型態 .............................. 3 第二章 黃皮屬植物之研究概況 .................. 5 第一節 黃皮屬植物之藥理研究回顧 ............ 5 第二節 黃皮屬植物之成分研究回顧 ........ 7 第三章 過山香根部萃取與分離 .............. 24 第四章 成分之構造研究 ..................... 29 第一節Clausenanine-A (246)之構造研究 ................................................................. 29 第二節Clausenanine-B (247)之構造研究 ................................................................. 33 第三節2-Hydroxy-6,8-dimethoxy-9H-carbazole-3-carbaldehyde (30)之構造研究 . 37 第四節Clausenatine-A (244)之構造研究 .................................................................. 40 第五節N-(γ, γ-dimethylallyl)-1-methoxy-3-methylcarbazole (245)之構造研究 ...... 44 第六節Clausenanine-C (248)之構造研究 ................................................................. 48 第七節Clausebismine-A (249)之構造研究 ............................................................... 52 第八節Clausebismine-B (250)之構造研究 ............................................................... 56 第九節Clausebismine-C (251)之構造研究 ............................................................... 60 第十節Clausebismine-D (252)之構造研究 .............................................................. 64 第十一節5-O-Acetyl clausarin (258)之構造研究 ..................................................... 68 第十二節Bisnorponcitrin (257)之構造研究 ............................................................. 72 第十三節Clausenaabismarin-A (259)之構造研究 .................................................... 76 第十四節Clausecavine-A (254)之構造研究 ............................................................. 81 第十五節 Clausetrimine-A (253)之構造研究 ........................................................... 85 第十六節 其他化合物之構造決定 ................. 87 第五章 結論 ................ 88 第六章 實驗部分 ............................. 90 第一節 本實驗所使用之儀器和藥品 ........... 90 第二節 植物之採集與鑑定 .................. 90 第三節 過山香根部之萃取與分離 ............. 91 光譜數據 ............ 93 參考文獻 .................... 122

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