- 學位論文
台灣產固有種植物–屏東花椒及細葉茶梨之化學成分與生物活性之研究
Chemical constituents and biological activities from endemic plants of Zanthoxylum wutaiense and Anneslea fragrans var. lanceolata
摘要
從1400種台灣產之原生或固有種植物抽出物做各種活性之篩選，發現屏東花椒之根材與莖材具有抗結核活性、細葉茶梨之根部具有抗氧化之活性。屏東花椒之根材先前已有16個新化合物被分離出來；本次研究除了繼續根材及莖材之化學成分之研究外，且對這兩種台灣固有種植物做活性探討。 從台灣產固有種屏東花椒根材部分離出五個新化合物，分別為：wutaipyranol A (574)、8-methoxywutaipyranol A (575)、demethoxywutaiensal (576)、demethoxywutaiensol (577)和dihydrodemethoxywutaiensol (578)及二十一個已知化合物。從莖材部，目前已分離得到八個新化合物，分別為：wutaienmol (579)、7-methoxyanodendroic acid (580)、trans-demethoxywutaiensic acid (581)、cis-demethoxywutaiensic acid (582)、(2'S,2'S,7S,8S)-wutaienin (584)、(2'S,2'S,7R,8R)- wutaienin(585)、(2'S,2'S,7S,8S)-wutaienin methyl ether (586)、(2'S,2'S,7R,8R)-wutaienin methyl ether (587)，一個天然首次分離化合物：4-hydroxy-3-(3-methylbut-2-enyl)benzaldehyde (583)，與二十七個已知化合物。其中584-587是以C-8/9'-鍵結之 neolignan type新骨架化合物；這些化合物透過日本千葉大學Ishikawa教授利用不齊合成來決定其立體。從根皮部分離出三十一個已知化合物。這些化合物之構造藉由一維和二維的核磁共振光譜，以及質譜而證明。其中化合物中：123, 125, 414, 539, 542, 552, 576針對於結核菌Mycobacterium tuberculosis H37Rv有顯著的抗結核活性。 從台灣產固有種細葉茶梨根部分離出四個新化合物，分別為davidigenin-2'-O-(6'-O-4'-hydroxybenzoyl)-b-glucoside (588)、davidigenin-2'-O-(2'-O-4'-hydroxybenzoyl)-??-glucoside (589)、davidigenin-2'-O-(3'-O-4'- hydroxybenzoyl)-b-glucoside (590)、davidigenin-2'-O-(6'-O-syringoyl)-b-glucoside (591)，以及十五個已知化合物。其中化合物： 23、91、588和591顯示對於ABTS [2,2′-azino-bis-(3-ethyl- benzthiazoline-6-sulfonic acid)] 自由基清除率 SC50 值在二十分鐘分別為 27.5、6.0、52.6及26.0 ug/mL。23、59、91 及顯示對於DPPH [1,1-diphenyl-2- picrylhydrazyl] 自由基清除率 SC50值在三十分鐘分別為 4.3、51.6及8.4 ug/mL。
並列摘要
About 1400 species of Formosan plants have been screened for biological activities in our laboratory. Among them, the root wood and stem wood of Zanthoxylum wutaiense Chen (Rutaceae) showed the antitubercular activities and the root of Anneslea fragrans Wall. var. lanceolata Hayata (Theaceae) showed the ABTS and DPPH radical scavenging activities. There were 12 new compounds were reported from the root wood of Z. wutaiense. The aims of this study are to complete the chemical constituents of Z. wutaiense, and evalute the active constituents of two endemic plants. Five new compounds, wutaipyranol A (574), 8-methoxywutaipyranol A (575), demethoxywutaiensal (576), demethoxywutaiensol (577), and dihydrodemethoxy- wutaiensol (578), together with twenty one known compounds were isolated from the root wood of Z. wutaiense. Eight new compounds, wutaienmol (579), 7-methoxyanodendroic acid (580), trans-demethoxywutaiensic acid (581), cis-demethoxywutaiensic acid (582), (2'S,2'S,7S,8S)-wutaienin (584), (2'S,2'S,7R,8R)- wutaienin(585), (2'S,2'S,7S,8S)-wutaienin methyl ether (586), (2'S,2'S,7R,8R)-wutaienin methyl ether (587), and one isolated for the first time from nature, 4-hydroxy-3-(3-methylbut-2-enyl)benzaldehyde (583), together with twenty seven known compounds were isolated from stem wood of this species. Among them, 584-587 were novel neolignans which were linked from C-8 to C-9' by a C-C bond directely, and these compounds have been identified with synthetic products via asymmetric synthesis. In addition, thirty-one known compounds were isolated from the root bark of this species. Among the isolates, 123, 125, 414, 539, 542, 552, and 576 exhibited antitubercular activities against Mycobacterium tuberculosis H37Rv in vitro. Four new compounds, davidigenin-2'-O-(6'-O-4'-hydroxybenzoyl)-b-glucoside (588), davidigenin-2'-O-(2'-O-4'-hydroxybenzoyl)-??-glucoside (589), davidigenin-2'-O-(3'-O-4'-hydroxybenzoyl)-b-glucoside (590), davidigenin-2'-O-(6'-O-syringoyl)-b-glucoside (591), and fifteen known compounds were isolated from the root of Anneslea fragrans var. lanceolata Hayata. 23, 91, 588, and 592 showed ABTS cation radical scavenging activity, with SC50 values of 27.5, 6.0, 52.6, and 26.0 ug/mL in 20 min, respectively. 23, 59, and 91 showed the DPPH radical scavenging activity, with SC50 values of 4.3, 51.6, and 8.4 ug/mL in 30 min, respectively.
參考文獻
延伸閱讀
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