复叶地黄连化学成分及其抗烟草花叶病毒活性研究

Chemical constituents from Munronia henryi and their anti-TMV activity

目的为进一步寻找具有较强抗烟草花叶病毒(tobacco mosaic virus,TMV)活性的柠檬苦素类化合物,开展复叶地黄连Munronia henryi化学成分研究。方法综合运用硅胶柱色谱、C18柱色谱、Sephadex LH-20凝胶柱色谱以及高效液相色谱等方法进行系统分离和纯化,根据化合物的理化性质及其波谱数据进行结构鉴定,采用半叶枯斑法,从钝化活性、保护活性、治疗活性3方面评估化合物1~13的抗TMV活性。结果从复叶地黄连的甲醇提取物中分离得到了13个化合物,分别鉴定为nymania-3(1)、prieurianin(2)、munronin L(3)、12-O-methylvolkensin(4)、12-hydroxyisopimara-8(14),15-dien-7-one(5)、munroninR(6)、3β,4β-dihydroxypregnan-16-one(7)、(E)-aglawone-3-one(8)、N-(N-benzoyl-S-phenylalaninyl)-Sphenylalaninol acetate(9)、N-(N-benzoyl-S-phenylalaninyl)-S-phenylalaninol benzoate(10)、glabrol(11)、syringaresinol(12)、7-methoxy-8-hydroxydihydroasarone(13)。其中化合物1对TMV的半数抑制浓度(IC50)为17.2μg/m L。结论化合物5、7~13为首次从该植物中分离得到,化合物1~3、5、9~12具有较强的抗TMV活性,其活性高于阳性对照药物宁南霉素。

Objective To find limonoids which had strong resistance activity against tobacco mosaic virus(TMV),so as to further screen the better active compounds and study the chemical compositions from Munronia henryi.Methods The chemical constituents from the whole plants of M.henryi were separated and purified by silica gel,C18,Sephadex LH-20 gel column chromatographies and HPLC,and their structures were identified by physiochemical properties and spectroscopic data.The anti-TMV activity of compounds 1—13 were evaluated by inoculating half leaf method from inactivation effect,protection effect and curative effect.Results Thirteen compounds were obtained from methanol extract from M.henryi and their structures were identified as nymania-3(1),prieurianin(2),munronin L(3),12-O-methylvolkensin(4),12-hydroxyisopimara-8(14),15-dien-7-one(5),munronin R(6),3β,4β-dihydroxypregnan-16-one(7),(E)-aglawone-3-one(8),N-(N-benzoyl-S-phenylalaninyl)-S-phenylalaninol acetate(9),N-(N-benzoyl-S-phenylalaninyl)-S-phenylalaninol benzoate(10),glabrol(11),syringaresinol(12)and 7-methoxy-8-hydroxydihydroasarone(13).The minimum half inhibition concentration(IC50)of compound 1 against TMV was 17.2μg/mL.Conclusion The compounds 5 and 7—13 are isolated from this plant for the first time.Compounds 1—3,5,and 9—12 have strong anti-TMV activity,which is higher than positive contrast of ningnanmycin.