相思樹莖皮化學成分及其生物活性之研究

相思樹(Acacia confusa)，為台灣的原生種植物，廣泛分布在台灣，在二次林和荒地是很常見的植物。相思樹常被種植當作防風林使用，木材可製成火車軌道的枕木，或是當作煤炭。相思樹也是一種台灣的傳統中草藥，用於治療血循環障礙。在我們一系列對於豆科植物的生物活性代謝物的研究中，發現相思樹莖皮的甲醇萃取物，具有抗C型肝炎病毒的活性。在本研究中，將相思樹莖皮的甲醇萃取物，經過分配萃取得到四個分層，分別為水層、正丁醇層、75%甲醇水溶液層和正己烷層。依據活性導引分離法，從75%甲醇水溶液層總共分得四個新化合物，包括acacinol A(1), acacinol B(2), acaciacoumarin(3), epicatechin-(4β→8, 2β→O→7)- 3,5,7,3',5'-pentahydroxyflavan(23)，以及二十一個已知化合物，epiphyllocoumarin(4), phyllocoumarin(5), (+)-catechin(6), (-)-epicatechin(7), luteolin(8), catechin-3-α-O-rhamnopyranoside(9), quercetin-3-α-O-rhamnopyranoside(10), phloridzin(11), lyoniresinol(12), the mixture of (+)-lyoniresinol-9'-α-O-rhamnoside(13) and (-)-lyoniresinol-9'-α-O-rhamnoside (14), indole-3-carboxylic acid (15), indole-3-aldehyde(16), cucumegastigmane I (17), 3-(4-hydroxy-3-methoxyphenyl)-1,2-propanediol(18), 1,2-dihydroxy-4- methoxybenzene(19), vanillic acid (20), isovanillic acid(21), procyanidin A1 (22), procyanidin B2 (24) 和procyanidin B1(25)。所有化合物皆經由質譜及光譜資料等分析方法加以證明。分離出的純化合物進行抗C型肝炎病毒和細胞毒殺活性試驗。主量的化合物(6,7,9,10,13,14)無顯著的抗C型肝炎病毒和細胞毒殺活性。化合物11, 23, 24具有抗C型肝炎病毒的活性。

關鍵字

豆科；相思樹屬；相思樹；抗C型肝炎病毒

並列摘要

Acacia confusa (Leguminosae), a species indigenous to Taiwan, is throughout Taiwan, very common in secondary forest and wastelands. The plant can be served as windbreaks, and the wood is suitable for making railroad crossties and charcoal. A. confusa is also a kind of Taiwanese traditional herbal medicine for blood circulation disorders. Our continuing research on bioactive metabolites from Leguminous plants led us to investigate the methanol extract from stem barks of this plant, which was active toward anti-hepatitis C virus. In this study, the MeOH extract was partitioned into four layers, H2O, n-BuOH, aq. 75% MeOH, and n-heaxane layer, respectively. Bioassay-guided fractionation of the aq. 75% MeOH layer has led to the isolation of 4 new compounds, acacinol A(1), acacinol B(2), acaciacoumarin (3), epicatechin-(4β→8,2β→O→7)-3,5,7,3',5'- pentahydroxyflavan (23) together with 21 know compounds including, epiphyllocoumarin (4), phyllocoumarin (5), (+)-catechin (6), (-)-epicatechin (7), luteolin (8), catechin-3-α-O-rhamnopyranoside (9), quercetin-3-α-O-rhamnopyranoside (10), phloridzin (11), lyoniresinol (12), the mixture of (+)-lyoniresinol-9'-α-O-rhamnoside (13) and (-)-lyoniresinol -9'-α-O-rhamnoside (14), indole-3-carboxylic acid (15), indole-3-aldehyde (16), cucumegastigmane I (17), 3-(4-hydroxy-3-methoxyphenyl)- 1,2-propanediol(18), 1,2-dihydroxy-4-methoxybenzene (19), vanillic acid(20), isovanillic acid(21), procyanidin A1(22), procyanidin B2(24) and procyanidin B1(25). The structures of these compounds were identified by spectroscopy data and chemical methods. Pure compounds were tested for anti-HCV and cytotoxicity activities. The major compounds(6,7,9,10,13,14) show no significant activity toward anti-HCV and cytotoxicity toward HepG2, MDA-MB-231 and A549 cell lines. Compounds 11, 23, 24 showed anti-HCV activity.