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標題: 馬齒莧地上部分之生理活性成份分離研究
Bioactive Components Isolated from the aerial part of Portulaca oleracea Linn
作者: 陳雨琳
Chen, Yu-Lin
Contributors: 鍾婷婷
化學系所
關鍵字: 甲醇粗萃物;水可溶層;正丁醇可溶層;黃酮苷類;木酚素苷類;生理活性測試;luteolin-7-O-[β-D-glucopyranosyl(1→6)][β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl(1→2)]-β-D-glucopyranoside;apigenin-7-O-[β-D-glucopyranosyl(1→6)][β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl(1→2)]-β-D-glucopyranoside;5,5’-dimethoxy-7,7’-dihydroxy-9’-β-glucopyranosyloxyl secoisolariciresinol;apigenin-7-O-[β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl(1→2)]-β-D-glucopyranoside。
Portulaca oleracea Linn;the methanol extract;n-butanol soluble fraction;water soluble fraction;flavonoid glucosides;lignan glucosides;bioactive test;luteolin-7-O-[β-D-glucopyranosyl(1→6)][β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl(1→2)]-β-D-glucopyranoside;apigenin-7-O-[β-D-glucopyranosyl(1→6)][β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl(1→2)]-β-D-glucopyranoside;5,5’-dimethoxy-7,7’-dihydroxy-9’-β-glucopyranosyloxyl secoisolariciresinol;apigenin-7-O-[β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl(1→2)]-β-D-glucopyranoside.
日期: 2013
Issue Date: 2013-11-07 13:21:48 (UTC+8)
Publisher: 化學系所
摘要: 本實驗將馬齒莧(Portulaca oleracea Linn)地上部分以甲醇浸泡萃取,過濾後經減壓濃縮得到的甲醇粗萃物溶於水,分別與正己烷、正丁醇做分配萃取,得到各粗分配層。本實驗進行水可溶層和正丁醇可溶層成分之單離與鑑定。
利用大孔吸附樹脂層析法(Diaion HP-20)、膠體過濾法(Sephadex LH-20)及逆相ODS填充管柱等過程進行分離純化共得8個化合物,於水可溶層中分離得到5個化合物,分別為2個氫醌類(hydroquinones):gentisic acid 5-β-D-glucoside (PW1)、gentisic acid 5-α(β)-D-xylopyranoside (PW2);2個黃酮苷類(flavonoid glucosides):luteolin-7-O-[β-D-glucopyranosyl(1→6)][β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl(1→2)]-β-D-glucopyranoside (PW3)、apigenin-7-O-[β-D-glucopyranosyl(1→6)][β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl(1→2)]-β-D-glucopyranoside (PW4);1個木酚素類(lignan):5,5’-dimethoxy-7,7’-dihydroxy-9’-β-glucopyranosyloxyl secoisolariciresinol (PW5)。於正丁醇可溶層中分離得到3個化合物,分別為2個苯丙素類(phenylpropanoid):1-feruloyl-β-D-glucopyranoside (PB1)、caffeic acid (PB2);1個黃酮苷類(flavonoid glucosides):apigenin-7-O-[β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl(1→2)]-β-D-glucopyranoside (PB3),而其中化合物PW3、 PW4、 PW5、PB3為文獻中不曾報導之新化合物。
利用高效能液相層析儀進行定性分析,將馬齒莧地上部分萃取物之指紋圖譜與分離所得的八個標準品進行比對,其滯留時間分別為7.7 min (PW1)、11.2 min (PW2)、13.9 min (gentisic acid)、14.0 min (PB1)、14.4 min (PB2)、14.5 min (PW3)、16.1 min (PW4)、16.6 min (PW5)、19.5 min (PB3)。
在成分之活性測試中,結果顯示PB1和PB2對於人類腎臟癌細胞株(786-O)和老鼠腎纖維母細胞(NRK-49f)具有抑制效果,其致死之IC50數值:786-O細胞分別為590 μM、930 μM,NRK-49f細胞分別為760 μM、580 μM。
The methanol extract of the aerial part of Portulaca oleracea Linn was dissolved into water and partitioned successively with n-hexane, n-butanol. In this research, we focus on the bioactive compounds in the n-butanol and water soluble fractions. Which under went a series column chromatographies on macroporous resin chromatography (Diaion HP-20), gel filtration (Sephadex LH-20) and reverse phase ODS column to give eight compounds. Five compounds were isolated from water soluble fraction, two of those were hydroquinones type of compounds:gentisic acid 5-β-D-glucoside (PW1), gentisic acid 5-α(β)-D-xylopyranoside (PW2), two of those were flavonoid glucosides:luteolin-7-O-[β-D-glucopyranosyl(1→6)][β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl(1→2)]-β-D-glucopyranoside (PW3), apigenin-7-O-[β-D-glucopyranosyl(1→6)][β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl(1→2)]-β-D-glucopyranoside (PW4), and the fifth one is a lignan:5,5’-dimethoxy-7,7’-dihydroxy-9’-β-glucopyranosyloxyl secoisolariciresinol (PW5). Another three compounds were isolated in n-butanol soluble fraction, there were two phenylpropanoids including:1-feruloyl-β-D-glucopyranoside (PB1) and caffeic acid (PB2), one flavonoid glucoside:apigenin-7-O-[β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl(1→2)]-β-D-glucopyranoside (PB3). Among them four compounds, PW3, PW4, PW5, PB3 have not been reported from literature.
In addition, we studied the qualitative analysis of the ten compounds in n-butanol and water fractions of aerial part of Portulaca oleracea Linn by HPLC/UV. On the chromatogram, it showed eight peaks in accordance with the fingerprint of the methanol extract. Their retention times were as follow:7.7 min (PW1), 11.2 min (PW2), 13.9 min (gentisic acid), 14.0 min (PB1), 14.4 min (PB2), 14.5 min (PW3), 16.1 min (PW4), 16.6 min (PW5), 19.5 min (PB3).
Finally, the biological activity displayed that among the above compounds, PB1and PB2 showed inhibition on cell growth of renal cancer cells (786-O) and rat kidney fibroblasts (NRK-49f). The values of 50% cytotoxic concentration (IC50) of PB1are 590 and 760 μM, respectively. The values of IC50 of PB2 are 930 and 580 μM, respectively.
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