- 學位論文
金合歡根部化學及活性成分之研究
Chemical Constituents and Bioactivity of the Roots of Acacia farnesiana
摘要
金合歡Acacia farnesiana (L.) Willd.屬於豆科(Leguminosae) 含羞草亞科（Minosoideae），相思樹(Acacia)屬植物。本研究取其根部(8.5kg)，以甲醇連續萃取三次，其抽取液經減壓濃縮後，進行分配萃取,得到n-Hexane、CHCl3、H2O-A、H2O-B、H2O-C五層劃分層。 上述劃分層分別利用管柱層析，如矽膠(silica gel)，分子篩(Sephadex LH-20) 及高效能液相層析分析儀(HPLC)等，進行純化分離，共分離得到二十六個化合物。包括七個雙萜類: ent-Kauran-16β-ol (1)、ent-16α,17β-Dihydroxykaurane (2)、ent-kaur-16-ene-3β,13-diol (3)、 acasiane A (4)*、acasiane B (5)*、farnesirane A (6)*、farnesirane B (7)*，一個二胜肽化合物: aurantiamide acetate (8)，二個三萜類化合物: betulinic acid (9)、lupeol (10)，八個黃酮類化合物: apigenin (11)、4’,7-dimethoxyapigenin (12)、5’,4’-dihydroxy-7-methoxyflavone (13)、diosmetin (14)、7,4’-dihydroxyflavone (15)、3’,4’,5-trihydroxy- 7-methoxyflavone (16)、luteolin (17)、luteolin-4’,7-dimethyl ether (18)，四個苯環類化合物: methyl 3, 4-dihydroxybenzoate (19)、4-hydroxybenzaldehyde (20)、syringaldehyde (21)、vanillin (22)，四個固醇類化合物: β-sitosterol (23) 與stigmasterol (24) 混合物、β-sitosterol-3-O-β-D-glucoside (25) stigmasterol-3-O-b-D-glucoside (26) 混合物。上述化合物之構造係利用其物化性質及NMR和MS等光譜資料來決定。所分離得到之化合物中，化合物4~5、6~7為新化合物。 在生物活性方面，化合物2、9對肝癌細胞Hep 3B具有選擇性的細胞毒殺的作用，化合物8和13對肺癌細胞A549具有選擇性的細胞毒殺作用，而化合物10則對口腔癌細胞Ca9-22具有選擇性的細胞毒殺作用。
並列摘要
Acacia farnesiana (L.) Willd. belongings to Minosoideae subfamily. In this study, the roots (8.5 kg) of this plant were collected and extracted by MeOH. The extract was dried and partitioned to five layers (n-Hexane, CHCl3, H2O-A, H2O-B, H2O-C). Chromatographic separation was processed with silical gel, Sephardex, and HPLC purification. Twenty-six compounds were afforded includ seven diterpenoids: ent-Kauran-16β-ol (1), ent-16α,17β-Dihydroxykaurane (2), ent-kaur -16-ene-3β,13-diol(3), acasiane A (4), acasiane B (5), farnesirane A (6), and farnesirane B (7) ; one dipeptied : aurantiamide acetate (8); two triterpenoids : betulinic acid (9) and lupeol (10) ; eight flavonoids: apigenin (11), 4’,7-dimethoxyapigenin (12), 5’,4 -dihydroxy-7-methoxyflavone (13), diosmetin (14), 7,4’-dihydroxy -flavone (15), 3’,4’,5-trihydroxy-7 -methoxyflavone (16), luteolin(17), and luteolin-4’,7-dimethyl ether(18) ; four benzenoids : methyl 3, 4-dihydroxybenzoate (19), 4-hydroxybenzaldehyde (20), syringaldehyde (21), and vanillin (22) ; four steroids : a mixture of β-sitosterol (23) and stigmasterol (24) and a mixture of β-sitosterol-3-O-β-D-glucoside (25) and stigmasterol-3-O-b-D -glucoside (26). The structures of these compounds were elucidated by physical and chemical data as well as NMR and MS spectroscopic analyses. The the isolates separation, 4, 5, 6 and 7 are new. Compounds 2 and 9 showed significant cytotoxicity activity toward to the Hep 3B liver cancer cell line; compounds 8 and 13 presented bioactivity agonist to the A549 cancer cell line. Moreover, compound 10 showed selected activity toward to the Ca9-22 oral cancer cell line.