黔产牛耳朵正丁醇部位中1个新的齐墩果烷型三萜糖苷OA
A new oleanane-type triterpenoid glycoside from n-butanol fraction of Primulina eburnea from Guizhou
目的 研究牛耳朵Primulina eburnea正丁醇部位的化学成分及其抗氧化和抗炎活性.方法 运用正、反相硅胶柱色谱、Sephadex LH-20 凝胶柱色谱与RP-HPLC等色谱学技术对化合物进行分离纯化,并结合NMR、UV、IR等光谱学技术对其结构进行鉴定.进一步利用 1,1-二苯基-2-三硝基苯肼自由基(1,1-diphenyl-2-picrylhydrazyl,DPPH)法和总抗氧化能力检测试剂盒[total antioxidant capacity(T-AOC)assay kit,ABTS]法评价所得化合物的抗氧化活性,采用Griess法检测化合物对脂多糖(lipopolysaccharide,LPS)诱导RAW264.7 细胞产生NO的影响来评估其抗炎活性.结果 从牛耳朵正丁醇部位中分离得到 20 个化合物,分别鉴定为火焰木酸-28-O-β-D-龙胆二糖苷(1)、木通苯乙醇苷B(2)、2-(3,4-二羟基苯基)乙醇葡萄糖苷(3)、红景天苷(4)、酪醇(5)、6-hydroxyapigenin-7-O-β-[2-O-β-xyloglucoside](6)、淫羊藿醇A2(7)、(+)-异落叶松脂素(8)、5-甲氧基-(+)-异落叶松脂素(9)、(+)-丁香脂素-4'-O-β-D-吡喃葡萄糖苷(10)、二氢菜豆酸(11)、(6S,9R)-长寿花糖苷(12)、七叶内酯(13)、对羟基苯甲酸(14)、原儿茶酸(15)、香草酸(16)、丁香酸(17)、咖啡酸(18)、咖啡酸甲酯(19)、3-O-β-D-吡喃葡萄糖基-4-羟基咖啡酸甲酯(20).化合物 7、17 和 18 表现出显著的抗氧化活性.化合物 3、5～9 对LPS诱导的RAW264.7 细胞中NO的生成有显著的抑制作用.结论 化合物 1 为新的三萜糖苷类,命名为牛耳朵苷A,化合物 4、6、7、9～12、14、15和 20 为报春苣苔属植物首次分得,化合物 17 和18 为牛耳朵植物中首次分得,且部分化合物表现出显著抗氧化和抗炎活性.
Objective To study the chemical constituents,antioxidant activity and anti-inflammatory activity of the n-butanol fraction from Primulina eburnea.Methods Compounds were separated and purified using chromatographic techniques such as normal-phase and reversed-phase silica gel column chromatography,Sephadex LH-20 gel column chromatography and RP-HPLC.Meanwhile,their structures were identified by spectroscopic techniques including NMR,UV and IR.Subsequently,the antioxidant activities of obtained compounds were evaluated by the DPPH and ABTS assays,while the Griess assay was employed to determine the effect of these compounds on NO production in lipopolysaccharide(LPS)-induced RAW264.7 cells to assess their anti-inflammatory activity.Results A total of 20 compounds were isolated from the n-butanol fraction of P.eburnea and were respectively identified as spathodic acid-28-O-β-D-gentiobioside(1),calceolarioside B(2),2-(3,4-dihydroxyphenyl)ethanol glucoside(3),salidroside(4),tyrosol(5),6-hydroxyapigenin-7-O-β-[2-O-β-xyloglucoside](6),icariol A2(7),(+)-isolariciresinol(8),5-methoxy-(+)-isolariciresinol(9),(+)-syringaresinol-4'-O-β-D-glucopyranoside(10),dihydrophaseic acid(11),(6S,9R)-roseoside(12),esculetin(13),p-hydroxybenzoic acid(14),protocatechuic acid(15),vanillic acid(16),syringic acid(17),caffeic acid(18),caffeic acid methyl ester(19)and methyl-3-O-β-D-glucopyranosyl-4-hydroxy caffeic acid(20).Meanwhile,compounds 7,17 and 18 exhibited significant antioxidant activity.Compounds 3,5-9 exhibited significant inhibitory effects on the production of NO in LPS-induced RAW264.7 cells.Conclusion Compound 1 is a new triterpenoid glycoside,named eburneoside A.While compounds 4,6,9-12,14,15 and 20 were isolated for the first time from the genus Primulina.Additionally,compounds 17 and 18 were firstly isolated from P.eburnea.Furthermore,some of these compounds exhibited significant antioxidant and anti-inflammatory activities.
HUANG Hongying;CHEN Junlei;LIU Siyan;CHEN Quan;CHEN Xingxin;CHEN Xianrong;HAO Xiaojiang;GU Wei
State Key Laboratory of Discovery and Utilization of Functional Components in Traditional Chinese Medicine,Natural Products Research Center of Guizhou Province,School of Pharmaceutical Sciences,Guizhou Medical University,Guiyang 550014,ChinaState Key Laboratory of Discovery and Utilization of Functional Components in Traditional Chinese Medicine,Natural Products Research Center of Guizhou Province,School of Pharmaceutical Sciences,Guizhou Medical University,Guiyang 550014,ChinaState Key Laboratory of Discovery and Utilization of Functional Components in Traditional Chinese Medicine,Natural Products Research Center of Guizhou Province,School of Pharmaceutical Sciences,Guizhou Medical University,Guiyang 550014,ChinaState Key Laboratory of Discovery and Utilization of Functional Components in Traditional Chinese Medicine,Natural Products Research Center of Guizhou Province,School of Pharmaceutical Sciences,Guizhou Medical University,Guiyang 550014,ChinaState Key Laboratory of Discovery and Utilization of Functional Components in Traditional Chinese Medicine,Natural Products Research Center of Guizhou Province,School of Pharmaceutical Sciences,Guizhou Medical University,Guiyang 550014,ChinaState Key Laboratory of Discovery and Utilization of Functional Components in Traditional Chinese Medicine,Natural Products Research Center of Guizhou Province,School of Pharmaceutical Sciences,Guizhou Medical University,Guiyang 550014,ChinaState Key Laboratory of Discovery and Utilization of Functional Components in Traditional Chinese Medicine,Natural Products Research Center of Guizhou Province,School of Pharmaceutical Sciences,Guizhou Medical University,Guiyang 550014,ChinaState Key Laboratory of Discovery and Utilization of Functional Components in Traditional Chinese Medicine,Natural Products Research Center of Guizhou Province,School of Pharmaceutical Sciences,Guizhou Medical University,Guiyang 550014,China
医药卫生
苦苣苔科牛耳朵三萜糖苷抗氧化活性抗炎活性牛耳朵苷A红景天苷淫羊藿醇A2丁香酸
GesneriaceaePrimulina eburnea(Hance)Yin Z.Wangtriterpenoid glycosideantioxidant activityanti-inflammatory activityeburneoside Asalidrosideicariol A2syringic acid
《中草药》 2026 (1)
13-23,11
贵州省自然科学基金重点项目(黔科合基础-ZK[2024]重点084)
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