醴肠化学成分及其抗沙门菌T3SS的活性成分研究  

Chemical constituents from whole herbs of Eclipta prostrata and active components inhibit T3SS of Salmonella

作　　者：张晓春 鲁春华 ZHANG Xiao-chun;LU Chun-hua(Institute of Natural Medicinal Chemistry,School of Pharmaceutical Sciences,Cheeloo College of Medicine,Shandong University,Jinan 250012,China)

机构地区：[1]山东大学齐鲁医学院,山东大学药学院天然药物化学研究所,山东济南250012

出　　处：《中草药》2022年第16期4940-4947,共8页Chinese Traditional and Herbal Drugs

基　　金：国家自然科学基金面上项目(22177062);教育部创新团队项目(IRT_17R68)。

摘　　要：目的 研究醴肠Eclipta prostrata的化学成分及其抗沙门菌Ⅲ型分泌系统(type Ⅲ secretion system,T3SS)活性。方法 综合运用SephadexLH-20凝胶、正相硅胶、HPLC、中压反相等柱色谱方法进行分离纯化,MS、NMR、UV、IR等技术进行结构鉴定,采用SDS-PAGE法检测化合物1~18抗沙门菌T3SS毒力蛋白分泌活性。结果 从醴肠全草提取物中分离到18个化合物,分别鉴定为香豌豆酚(1)、3′-O-甲基香豌豆酚(2)、蟛蜞菊内酯(3)、异去甲蟛蜞菊内酯(4)、木犀草素(5)、5′-(4-羟基-1-丁炔-1-基)[2,2′-联噻吩]-5-醛(6)、α-三联噻吩(7)、α-三联噻吩甲醛(8)、α-三联噻吩甲醇(9)、5-甲氧亚甲基-2,2′:5′,2′′-三联噻吩(10)、5-羟甲基-(2,2′:5′,2′′)-三联噻吩乙酯(11)、[2,2′:5′,2′′-三联噻吩]-5-基甲基-2-甲基丁酯(12)、5-羟甲基-(2,2′:5′,2′′)-噻吩当归酸酯(13)、5-羟甲基-(2,2′:5′,2′′)-噻吩巴豆酸酯(14)、(Z)-[2,2′-联噻吩]-5-甲醇-5′-(3-丁烯-1-炔基)-2-巴豆酸酯(15)、(E)-5′-(3-丁烯-1-炔基)-[2,2′-噻吩]-5-甲醇-2-甲基巴豆酸酯(16)、5′-(3-丁烯-1-炔-1-基)-[2,2′-联噻吩]-5-甲醇-5-乙酯(17)和5′-羟甲基-5-(3-丁烯-1-炔基)-2,2′-联噻吩(18)。结论 化合物6、15、16首次从植物醴肠中分离得到。化合物5具有较强的沙门菌T3SS毒力蛋白分泌抑制活性,化合物1、3、4具有一定的抗T3SS活性,为醴肠民间用作排脓、止血、治热痢以及抗菌抗感染药物提供了科学的理论基础。Objective To investigate the chemical constituents and anti-T3SS activity from whole herbs of Eclipta prostrata.Methods The chemical constituents were systematically separated and purified by Sephadex LH-20,Silica gel,MPLC and HPLC column chromatography,and identified based on their MS and NMR data.The anti-T3SS activities of compounds 1—18 on Salmonella were detected by SDS-PAGE assay.Results Eighteen compounds were obtained from the extracts of E.prostrata and identified as orobol(1),3′-O-methyl orobol(2),wedelolactone(3),isodemethyl wedelolactone(4),luteolin(5),5′-(4-hydroxy-1-butyn-1-yl)[2,2′-bithiophene]-5-carboxaldehyde(6),α-terthienyl(7),α-formylterthienyl(8),α-terthienyl methanol(9),5-(methoxymethyl)-2,2′:5′,2′′-terthiophene(10),5-hydroxymethyl-(2,2′:5′,2′′)-terthienyl acetate(11),[2,2′:5′,2′′-terthiophen]-5-yl methyl 2-methylbutanoate(12),5-hydroxymethyl-(2,2′:5′,2′′)-terthienyl angelate(13),5-hydroxymethyl-(2,2′:5′,2′′)-terthienyl tiglate(14),(Z)-5′-(3-buten-1-ynyl)-[2,2′-bithiophene]-5-methanol-2-methylcrotonate(15),(E)-5′-(3-buten-1-ynyl)-[2,2′-bithiophene]-5-methanol-2-methylcrotonate(16),5′-(3-buten-1-yn-1-yl)-[2,2′-bithiophene]-5-methanol-5-acetate(17),and 5′-hydroxymethyl-5-(3-buten-1-ynyl)-2,2′-bithiophene(18),respectively.Conclusion Compounds 6,15 and 16 are isolated from this plant for the first time.Compound 5 has significant anti-T3SS activity against the effector protein secretion,meanwhile,compounds 1,3 and 4 showed certain activity,which provide a theoretical basis for the folk use of E.prostrata as purulent,hemostatic,heat dysentery,antibacterial and anti-infective drugs.

关 键 词：醴肠 抗沙门菌T3SS活性 抗毒力药物 噻吩 黄酮 5′-(4-羟基-1-丁炔-1-基)[2 2′-联噻吩]-5-醛 (Z)-[2 2′-联噻吩]-5-甲醇-5′-(3-丁烯-1-炔基)-2-巴豆酸酯 木犀草素 

分 类 号：R284.1[医药卫生—中药学]