相思樹心材化學成分及其生物活性之研究

Studies on the Chemical Constituents and Biological Activity of the Heartwoods of Acacia confusa

邱清毅(Ching-Yi Chiou)

指導教授 ： 吳永昌

高雄醫學大學/藥學院/天然藥物研究所碩士班/碩士(2009年)

摘要

豆科(Leguminosae)植物相思樹(Acacia confusa Merr.)，為多年生常綠喬木，分佈於亞洲地區，為台灣原生種。
以甲醇萃取相思樹心材獲得粗萃物，進行分配萃取得到正己烷層、正丁醇層、水層以及不溶物等四個劃分，其中正丁醇層具有抗C型肝炎病毒之活性，故選擇此層做進一步活性研究分析。
經吸附樹脂、分子篩、矽膠管柱層析與高效能液相層析儀分離純化，從正丁醇層共分離得到二十六個化合物，分別為十三個flavonoids，Acacidin A (1)、Acacidin B (2)、2R,3R,4R-4'-Methoxy- mollisacacidin (3)、2R,3R,4R-4'-Methoxy-3,3',4,7,8-penta- hydroxyflavan (4)、Huazhongilexone (5)、Isoliqiritigenin (6)、Myricetin 3-O-??-glucopyranoside (7)、Myricetin 3-O-??-rhamnopyranoside (8)、 (+)-Dihydroquercetin (9)、Quercetin (10)、Luteolin (11)、Kaempferol(12)、 3,7,8,3'-Tetrahydroxy-4'-methoxyflavone(13)，八個cerebrosides， 1-O-??-Glucopyranosyl- (2S,3R,4E,8Z)-2-N-[(2'R)- hydroxyhexadecanoyl]-4,8-octadecadiene-1,3-diol (14)、1-O-??- Glucopyranosyl-(2S,3R,4E,8E)-2-N-[(2'R)-hydroxyhexadecanoyl]-4,8-octadecadiene-1,3-diol (15)、 Acaciconoside A (16)、Acaciconoside B (17)、Acaciconoside C (18)、Acaciconoside D (19)、Acaciconoside E (20)、Acaciconoside F (21)，一個lignan， Lyonirsinol (22)，二個neolignans，Guajacylglycerin-??- coniferylether (23)、Guajacylglycerin-??-dihydroconiferylether (24)， 二個glycerols， 1-(24-Hydroxytetracosanoyl)glycerol (25)與1-(26-Hydroxyhexa- cosanoyl)-glycerol (26) 混合物。
其中化合物1跟2為新骨架化合物，而化合物3、16、17、18、19、20、21為新化合物，所分離之化合物皆經由質譜及光譜資料等分析方法加以證明。
在抗C型肝炎病毒活性中，化合物16、19和20顯示不錯的C型肝炎病毒抑制活性，其中化合物19在濃度2.5 ?嵱的濃度下仍有超過百分之五十的抑制活性。

關鍵字

相思樹 ； C型肝炎 ； 抗血小板凝集 ； 細胞毒殺

並列摘要

Acacia confusa Merr. (Leguminosae), an evergreen trees and indigenous to Taiwan, is widely distributed on the Asia.
In present study, the heartwoods of Acacia confusa were collected and extracted with methanol. The extract was then partitioned to four fractions (n-hexane layer, n-BuOH layer, H2O layer and insoluble residue), among them, the n-BuOH layer showed anti HCV activity. Therefore, the subject was selected for further investigating in development of new anti hepatitis C virus agents.
The n-BuOH layer further separated by column chromatography (macroporous adsorbent resin, sephadex, silica gel) and high performance liquid chromatography, and gave twenty-six compounds, including thirteen flavonoids, Acacidin A (1), Acacidin B (2), 2R,3R,4R-4'-Methoxy-mollisacacidin (3), 2R,3R,4R-4'-Methoxy-3,3',4,7,8-pentahydroxyflavan (4), Huazhongilexone (5), Isoliqiritigenin (6), Myricetin 3-O-??-glucopyranoside (7), Myricetin 3-O-??-rhamno-pyranoside (8), (+)-Dihydroquercetin (9), Quercetin (10), Luteolin (11), Kaempferol (12), 3,7,8,3'-Tetrahydroxy-4'-methoxyflavone (13); eight cerebrosides, 1-O-??-Glucopyranosyl-(2S,3R,4E,8Z)-2-N- [(2'R)-hydroxypalmitoyl]-4,8-octadecadiene-1,3-diol (14), 1-O-??- Glucopyranosyl-(2S,3R,4E,8E)-2-N-[(2'R)-hydroxypalmitoyl]-4,8-
octadecadiene-1,3-diol (15), Acaciconoside A (16), Acaciconoside B (17), Acaciconoside C (18), Acaciconoside D (19), Acaciconoside E (20), Acaciconoside F(21); one lignan， Lyonirsinol (22); two neolignans, Guajacylglycerin-??-coniferylether (23), Guajacylglycerin- ??-dihydroconiferylether (24); two glycerols, mixtures of 1-(24- Hydroxytetra-cosanoyl)glycerol (25) and 1-(26-Hydroxyhexa- cosanoyl)-glycerol (26).
Among them, the structures of compounds 1 and 2 are new skeleton, and compounds 3, 16, 17, 18, 19, 20, 21 are new. Structures of isolates were elucidated by spectroscopic data and chemical methods.
Compounds 16, 19, 20 showed better inhibitory effects on anti-HCV activity than the other compounds, among them, compound 19 has 52% inhibition at the concentration of 2.5 mM .

並列關鍵字

Acacia confusa ； HCV ； Anti-platelet aggregation ； Cytotoxicity

參考文獻

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