沉香屬(瑞香科)的植物廣泛分布在亞洲，過去對中國沉香的植物化學研究顯示出主要基團是由倍半帖烯和2-(2-苯乙基)色酮衍生物所組成，但對於未植菌白木香(Aquilaria sinensis)的化學組成份所知甚少。本研究主要利用管柱層析法對從台灣北部產瑞香科植物—白木香之木材部及樹皮部進行成分研究，先將白木香蔭乾的木材及樹皮部以甲醇浸泡萃取，再使用正己烷、丙酮和甲醇等為溶媒以色層分析法分離。木材部共得到十二個化合物，包括四個黃酮類化合物，分別為5-羥基-7,4′-二甲氧基黃酮、5-羥基-7,3′,4′-三甲氧基黃酮、5,3′-二羥基-7,4′-二甲氧基黃酮和5,4′-二羥基-7,3′-二甲氧基黃酮；三個苯環類化合物，分別為香草酸、對羥基苯甲酸和丁香酸；一個苯二酚類化合物：4-乙醯基-3,5-二甲氧基-對苯二酚；二個醯胺類化合物，分別為N-反式-對羥基苯乙基阿魏醯胺和N-順式-對羥基苯乙基阿魏醯胺；一個木質酚類化合物：(+)-紫丁香樹脂酚及一個固醇類化合物：β-麥固脂酮。樹皮部共得到八個化合物，包括五個黃酮類化合物，分別為5-羥基-7,4′-二甲氧基黃酮、5,4′-二羥基-7-甲氧基黃酮、5-羥基-7,3′,4′-三甲氧基黃酮、5,3′-二羥基-7,4′-二甲氧基黃酮和5,4′-二羥基-7,3′-二甲氧基黃酮；一個苯環類化合物：對羥基苯甲酸甲酯；一個木質酚類化合物：(+)-紫丁香樹脂酚及一個固醇類化合物：β-穀固醇。以上所有化合物均為第一次由此種植物分離出來。另外從白木香摘取其中四個黃酮類化合物5-羥基-7,4′-二甲氧基黃酮、5,4′-二羥基-7-甲氧基黃酮、5-羥基-7,3′,4′-三甲氧基黃酮、5,3′-二羥基-7,4′-二甲氧基黃酮做黑色素瘤的抗癌活性試驗，結果顯示四個化合物的抗癌效果均隨劑量增加而增加。

Organisms in the genus Aquilaria (Thymelaeaceae) are widely distributed in Asia. Previous phytochemical investigation on Chinese agarwood revealed characteristic sesquiterpenes and chromone derivatives, but the chemical constituents in each part of the agarwood is not clear. The chemical constituents in the wood and bark of Aquilaria sinensis were separated with column chromatography. Twelve compounds, including four flavonoids, 5-hydroxy-7,4′-dimethoxyflavone, 5-hydroxy-7,3′,4′-trimethoxyflavone, 5,3′-dihydroxy-7,4′-dimethoxyflavone and 5,4′-dihydroxy-7,3′-dimethoxyflavone , three benzenoids, vanillic acid , p-hydroxybenzoic acid , and syringic acid , one quinol, 4-acetonyl -3,5-dimethoxy-p-quinol, two amides, N-trans-feruloyltyramine and N-cis-feruloyltyramine , one lignan, (+)-syringaresinol and one steroid, β-sitostenone were isolated from the wood of A. sinensis. Eight compounds, including five flavonoids, 5-hydroxy-7,4′-dimethoxyflavone, 5,4′-dihydroxy-7-methoxyflavone , 5-hydroxy -7,3′,4′-trimethoxyflavone , 5,3′-dihydroxy-7,4′-dimethoxyflavone and 5,4′-dihydroxy-7,3′-dimethoxyflavone , one benzenoid, methylparaben , one lignan, (+)-syringaresinol and one steroid, β-sitosterol were isolated from the bark of A. sinensis. All of these compounds were obtained for the first time from this plant. The anti-cancer activities of 5-hydroxy-7,4′-dimethoxyflavone, 5,4′-dihydroxy-7-methoxyflavone, 5-hydroxy-7,3′,4′-trimethoxyflavone, 5,3′-dihydroxy-7,4′-dimethoxyflavone on melanoma were examined. Results indicated that the anti-cancer effects of these four compounds increase with the increasing doses.

目 錄
論文審定書 …………………………………………………………..… i
誌謝 …………………………………………………………………..... ii
中文摘要……………………………………………………………….... iii
英文摘要……………………………………………………………........ v
目錄 …………………………………………………………….…..........vii
圖目錄……………………………………………………………………viii
表目錄……………………………………………………..………....….. ix
第一章 緒論 …………………………………………………………... 1
第一節 前言 ………………………………………………….….. 1
第二節 植物形態分佈與應用…..……………………................... 2
第三節 白木香化學成分之文獻回顧 ........................................... 4
第四節 研究目的與動機............................................................... 26
第二章 材料與方法 …………………………………………….…… 27
第一節 試驗材料 ………………………………………………. 27
第二節 白木香之分離與純化…………………………….…… ..30
第三節 白木香材部試驗流程……………………………….. ….33
第四節 白木香樹皮部試驗流程………………………………... 36
第三章 抗癌活性評估試驗 …………………………………………. 38
第一節 皮膚老化………..………………………………………. 38
第二節 抗癌活性評估目的………………………………..……. 40
第三節 抗癌活性試驗 …………………………………………. 41
第四章 結果 …………………………………………………………. 44
第一節 化合物之結構證明 ……………………………………. 47
第二節 5-hydroxy-7,4′-dimethoxyflavone 之結構證明 ............. 48
第三節 5-hydroxy-7,3′,4′-trimethoxyflavone 之結構證明........... 50
第四節 5,3′ -dihydroxy-7,4′-dimethoxyflavone 之結構證明....... 52
第五節 N-trans-feruloyltyramine 之結構證明 ........................... 54
第六節 (+)-syringaresinol 之結構證明......................................... 56
第七節 台灣北部產白木香成份之抽取與分離…………………58
第八節 化合物之氫光譜數據 ………………………...……….. 65
第九節 抗癌活性結果 ………………………………….…...…. 73
第五章 討論 ………………………………………..…………….….. 75
第六章 未來展望 ………………………………………….…….…... 81
第七章 參考文獻 ………………………………………….………… 83
第八章 論文著作及發表 …………………………………….……… 116

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