白饭树叶生物碱类成分及其抗乙酰胆碱酯酶活性研究

Studies on Alkaloids from the Leaves of Flueggea virosa and Their Acetylcholinesterase Inhibitory Activities

目的:研究白饭树叶的生物碱成分及其抗乙酰胆碱酯酶活性。方法:采用硅胶柱层析、MCI、Sephadex LH-20及半制备HPLC等色谱技术进行分离纯化,根据各种波谱学技术及X单晶衍射的方法对化合物进行结构鉴定,并通过Ellman的方法评价化合物的抗乙酰胆碱酯酶活性。结果:从白饭树叶中分离得到9个生物碱类化合物,分别鉴定为:4α-hydroxy-N-hydrogenallosecurinine chloride(1)、4-epiphyllanthine(2)、4α-hydroxy-15α-methoxy-14,15-dihydroallosecurinine(3)、4α-methoxy-phyllanthidine(4)、15β-methoxy-14,15-dihydrosecurinine(5)、securinine(6)、(+)-phyllanthidine(7)、14α-methoxy-13,14-dihydronorsecurinine(8)和fluevirine B(9)。化合物1和7终浓度为1 mg/m L时对乙酰胆碱酯酶的抑制率分别为27.2%和33.9%。结论:化合物1的核磁共振波谱数据及单晶结构为首次报道,化合物1、8、3~5为首次从该植物中分离得到,化合物1和7表现出一定的抗乙酰胆碱酯酶活性。

Objective:To research the alkaloids from the leaves of Flueggea virosa and their acetylcholinesterase(AChE)inhibitory activities.Methods :The compounds were isolated and purified by silica gel,MCI,SephadexLH-20column chromatographies and semipreparative HPLC,their structures were elucidated by analysis of the physicochemical properties,spectral data,and X-ray diffraction.AChE inhibitory activities were tested by Ellman's method.Results:Nine alkaloids were obtained from the leaves of Flueggea virosa and identified as 4a-hydroxy-N-hydrogenallosecurinine chloride (1),4-epiphyllanthine (2),4α-hydroxy-15α-methoxy-14,15-dihydroallosecurinine (3),4α-methoxy-phyllanthidine (4),15β-methoxy-14,15-dihydrosecurinine (5),securinine (6),(+)-phyllanthidine (7), 14α-methoxy-13,14-dihydronorsecurinine(8)and fluevirine B (9).Compounds 1 and 7 showed certain inhibition against AChE with the inhibition rate of 27.2%and 33.9%at a concentration of 1mg/mL,respectively.Conclusion:The NMR data and single-crystal structure of compound 1 are firstly reported.Compounds 1,8,and 3~5 are firstly obtained from this plant.Compounds 1 and 7 show certain AChE inhibitory activities.