华南胡椒的化学成分及其抗胆碱酯酶活性研究

Chemical Constituents of Piper austrosinense and Their Anticholinesterase Inhibitory Activity

采用凝胶树脂(Toyopearl HW-40c)、正相硅胶、反相硅胶(ODS)、大孔树脂(MCI)等柱层析方法和制备液相,从胡椒科胡椒属华南胡椒(Piper austrosinense)的茎叶的70%丙酮提取物中分离得到11个化合物,包括1个苯甲醛类衍生物(1),1个苯甲酸类衍生物(2)、2个苯丙素类成分(4和5)、2个黄酮苷(5和6)、2个生物碱(7和8)、2个倍半萜(9和10)、1个紫罗兰酮类(11)。运用波谱光谱学方法分别鉴定为:原儿茶醛(1),原儿茶酸(2),4-丙烯基儿茶酚(3),咖啡醛(4),青兰苷(5),野漆树苷(6),pipernonaline(7),吲哚-3-甲酸(8),4β,10β-二醇-香木兰烷(9)、(-)-丁香三环烷-2,9-二醇(10)、和(3S,5R,6S,7E)-3,5,6-三羟基-7-巨豆烯-9-酮(11)。其中,化合物5~11均首次从该植物中分离得到,化合物5,6,8~11均首次从胡椒属植物中分离得到。通过改良的Ellman法测试了所有化合物对乙酰和丁酰胆碱酯酶的抑制活性,测试结果表明化合物7显示选择性抑制丁酰胆碱酯酶的活性,半数抑制浓度(IC50)为29. 06±0. 32μM。其余化合物在30μM浓度下对乙酰和丁酰胆碱酯酶均不显示抑制活性。采用MTT法测试了所有化合物对肝癌细胞株(Hep G2)的体外细胞毒活性,测试表明所有化合物在30μM浓度下对所测试的细胞株未显示细胞毒活性。

Eleven compounds were isolated from the stem and leaf of Piper austrosinense by using the method of Toyopearl HW-40c,silica gel,ODS,MCI and pre-HPLC,including one benzaldehyde derivative,one benzoic acid derivative,three phenylpropanoids,two flavonoids,two alkaloids,two sesquiterpenes,and one ionone.The compounds were identified as protocatechualdehyde(1),protocatechuate(2),4-allyl catechol(3),caffeic aldehyde(4),cynaroside(luteolin-7-O-β-D-glucoside,5),rhoifolin(apigenin-7-O-neohesperidoside,6),pipernonaline(7),indole-3-formic acid(8),aromadendrane-4β,10β-diol(9),(-)-clovane-2,9-diol(10),and(3S,5R,6S,7E)-3,5,6-trihydroxy-7-megastigmen-9-one(11).Compounds 5-11 were firstly isolated from the title plant.Among them,it is the first time to report compounds 5,6,8-11 isolated in the genus Piper.In addition,compound 7 showed selective butyrylcholinesterase inhibitory activity with IC 50 value of 29.06±0.32μM,while other compounds showed no acetylcholinesterase and butyrylcholinesterase inhibitory activities at the concentration of 30μM.The cytotoxic activities of all compounds against HepG2 cell line were tested by MTT assay.However,no compounds showed cytotoxicity at the concentration of 30μM.