救必应中2个新的咖啡酸半萜酯  

Two new hemiterpenyl caffeates from bark of Ilex rotunda

作　　者：黄婉凤 何佳 张琛伟 何宇铭 王宝林 陆玫霖 陈明 冯育林 杨世林[1,2] 潘其明 高红伟[1] HUANG Wan-feng;HE Jia;ZHANG Chen-wei;HE Yu-ming;WANG Bao-lin;LU Mei-lin;CHEN Ming;FENG Yu-lin;YANG Shi-lin;PAN Qi-ming;GAO Hong-wei(College of Pharmacy,Guangxi University of Chinese Medicine,Nanning 530200,China;Jiangxi University of Traditional Chinese Medicine,Nanchang 330000,China)

机构地区：[1]广西中医药大学药学院,广西南宁530200 [2]江西中医药大学,江西南昌330000

出　　处：《中草药》2023年第8期2365-2372,共8页Chinese Traditional and Herbal Drugs

基　　金：广西中医药大学2020年博士科研启动基金项目(2020BS017)。

摘　　要：目的 研究铁冬青Ilex rotunda干燥树皮(救必应)的化学成分及其体外抗炎活性。方法 采用硅胶柱色谱、ODS柱色谱、D101大孔吸附树脂柱色谱和半制备高效液相色谱进行分离纯化,并运用HR-ESI-MS、NMR进行化合物结构鉴定。通过测定化合物对脂多糖(lipopolysaccharide,LPS)诱导小鼠RAW264.7巨噬细胞释放炎症介质一氧化氮(NO)的抑制能力,评价化合物的抗炎作用;MTT法测定化合物的细胞毒性。结果 从救必应中分离得到14个化合物,分别鉴定为咖啡酸[(E)-4-羟基-2-甲基丁-2-烯-1-基]酯(1)、咖啡酸[(E)-4-羟基异戊烯基]酯(2)、咖啡酸(4-羟基异戊烯基)酯β-D-吡喃葡萄糖苷(3)、rotundarpenoside B(4)、3,5-二咖啡酰基奎宁酸甲酯(5)、3,4-二咖啡酰基奎宁酸甲酯(6)、紫丁香苷(7)、芥子醛葡萄糖苷(8)、di-O-methylcrenatin(9)、咖啡酸(10)、芥子醛(11)、紫丁香醛(12)、原儿茶醛(13)、丁香酸(14)。结论 化合物1和2为2个新的咖啡酸半萜酯,分别命名为咖啡酸半萜酯A和咖啡酸半萜酯B。化合物3的氢谱和碳谱数据为首次报道。化合物1、2和11具有潜在的抗炎活性。Objective To investigate the chemical constituents from the dried bark of Ilex rotunda(“Jiu Bi Ying”in Chinese)and their anti-inflammatory activities.Methods The compounds of I.rotunda were isolated and purified by silica gel,ODS,D101 macroporous resin column chromatography and semi preparative-HPLC.The structures were elucidated via HR-ESI-MS and NMR spectroscopic data interpretation.The inhibitory rates of the isolated compounds against inflammatory cytokine nitric oxide(NO)production in LPS-stimulated mouse RAW264.7 macrophages were used to evaluate the anti-inflammatory activities.The cell viability was examined by the MTT assay.Results A total of 14 compounds were isolated from the bark of I.rotunda,their structures were elucidated as caffeic acid[(E)-4-hydroxy-2-methylbut-2-en-1-yl]-ester(1),caffeic acid[(E)-4-hydroxyprenyl]-ester(2),caffeic acid[4-hydroxyprenyl]-esterβ-D-glucopyranoside(3),rotundarpenoside B(4),methyl 3,5-dicaffeoylquinate(5),methyl 3,4-dicaffeoylquinate(6),syringin(7),sinapaldehyde glucoside(8),di-O-methylcrenatin(9),caffeic acid(10),sinapaldehyde(11),syringaldehyde(12),protocatechuic aldehyde(13),syringic acid(14).Conclusion Compounds 1 and 2 are two new caffeic acid hemiterpenyl esters,named as hemiterpenyl caffeate A and B,respectively.The 1H and 13C NMR spectra of compound 3 are reported for the first time.Compounds 1,2 and 11 showed potential anti-inflammatory activities.

关 键 词：救必应 苯丙素类化合物 咖啡酸半萜酯 紫丁香苷 抗炎活性 芥子醛 

分 类 号：R284.1[医药卫生—中药学]