中麻黄中2个新天然产物

Two new natural products of Ephedra intermedia

目的研究中麻黄Ephedra intermedia的化学成分。方法采用Toyopreal HW-40C、Sephadex LH-20、硅胶和半制备高效液相等多种色谱学技术分离得到单体化合物,并根据其理化性质和波谱学数据鉴定其结构,并通过建立C48/80诱导RBL-2H3细胞脱颗粒体外模型,对中麻黄中所得单体化合物进行体外抗哮喘活性筛选。结果从中麻黄50%丙酮提取物中分离得到21个化合物,分别鉴定为3-羟基-5-(4'-羟基苯基)戊酸乙酯(1)、3-羟基-5-(4'-羟基苯基)戊酸甲酯(2)、儿茶酚(3)、苯甲酸(4)、5-(4-羟基苯基)-2-戊烯酸(5)、(+)-rhododendrol(6)、frambinone(7)、香草乙酮(8)、4-羟基-3-甲氧基苯甲酸甲酯(9)、3,4-二羟基苯乙醇(10)、姜酮(11)、原儿茶酸(12)、3,5-二羟基-4-甲氧基苯甲酸(13)、丁香酸(14)、3-hydroxy-4-methoxy-benzene carboxylic acid(15)、香草酸(16)、丁香酸甲酯(17)、4-羟基-3-甲氧基苯丙酮(18)、去甲丁香色原酮(19)、5-(3,4-dihydroxyphenyl)-γ-valerolactone(20)、2-guaiacylpropane-1,3-diol(21)。对所得单体化合物进行体外抗哮喘活性筛选,结果显示,与模型组相比,在给药10μmol/L条件下,化合物5、18、19能够显著抑制β-氨基己糖苷酶的释放(P<0.05、0.01),化合物4、6、8、11、20、21能够轻微抑制β-氨基己糖苷酶的释放。结论化合物1和2为2个首次确定绝对构型的新天然产物,化合物3、5~15、17~21首次从该植物中分离得到,其体外抗哮喘活性筛选结果表明,在给药10μmol/L条件下,化合物5、18、19能够显著改善RBL-2H3脱颗粒现象,化合物4、6、8、11、20、21能够轻微改善RBL-2H3脱颗粒现象。

Objective To investigate chemical constituents of Ephedra intermedia.Methods The monomer compounds of this plant were isolated by various chromatographic techniques such as Toyopreal HW-40C,Sephadex LH-20,silica gel and semi-preparative HPLC.And their structures were determined by analysis of physicochemical properties and spectral data.The anti-asthma activities of these compounds from E.intermedia were evaluated by establishing an in vitro model of RBL-2H3 cells degranulation induced by C48/80.Results A total of 21 compounds were isolated from 50%acetone extract of E.intermedia,and identified as 3-hydroxy-5-(4'-hydroxyphenyl)ethyl valerate(1),3-hydroxy-5-(4'-hydroxyphenyl)methyl valerate(2),catechol(3),benzoic acid(4),5-(4-hydroxyphenyl)-2-pentenoic acid(5),(+)-rhododendrol(6),frambinone(7),acetovanillone(8),methyl-4-hydroxy-3-methoxybenzoate(9),3,4-dihydroxyphenylethanol(10),zingerone(11),protocatechuate(12),3,5-dihydroxy-4-methoxy-benzoic acid(13),syringic acid(14),3-hydroxy-4-methoxy-benzene carboxylic acid(15),vanillic acid(16),methyl syringate(17),4-hydroxy-3-methoxypropiophenone(18),noreugenin(19),5-(3,4-dihydroxyphenyl)-γ-valerolactone(20),2-guaiacylpropane-1,3-diol(21).The results of their anti-asthma activities showed that compounds 5,18,19(P<0.05,0.01)could significantly inhibit the release ofβ-hexosaminidase(β-Hex)at the concentration of 10μmol/L,and compounds 4,6,8,11,20,21 could slightly inhibit the release ofβ-Hex at the concentration of 10μmol/L.Conclusion Compounds 1 and 2 are two new natural products determined their absolute configurations for the first time,and compounds 3,5—15,and 17—21 were isolated from E.intermedia for the first time.The results of in vitro anti-asthma activities screening showed that compounds 5,18,19 could significantly improve RBL-2H3 degranulation,and compounds 4,6,8,11,20,21 could slightly improve RBL-2H3 degranulation at the concentration of 10μmol/L.