金樱子果实化学成分及其抗炎活性研究

Chemical constituents of Rosa laevigata fruits and their anti-inflammatory activities

关键词:  金樱子, 蔷薇属, 化学成分, 结构鉴定, 抗炎活性

Key words:   Rosa laevigata, Rosa, chemical constituents, structural identification, anti-inflammatory activity

摘要:

为阐明金樱子(Rosa laevigata)果实的化学成分及其抗炎活性,该研究以其乙醇提取物的乙酸乙酯部位为对象,经硅胶柱色谱及半制备高效液相色谱分离纯化,采用质谱、核磁共振等波谱学方法鉴定所得化合物的结构,并选取所得三萜类化合物,通过脂多糖(LPS)诱导的RAW264.7巨噬细胞一氧化氮(NO)生成抑制实验评价其抗炎活性。结果表明:(1)从乙酸乙酯部位共分离鉴定出19个化合物,分别鉴定为2α,3α,19α-三羟基-28-去甲乌苏-12-烯(1)、蔷薇酸(2)、1α,2β,3β,19α-四羟基乌苏-12-烯-28-酸(3)、2α,3α,19α,23-四羟基乌苏-12-烯-28-酸(4)、2α,3β,19α,23-四羟基乌苏-12-烯-28-酸(5)、刺梨苷F1(6)、hyptaic acid B(7)、银锻苷(8)、知母皂苷B(9)、楝叶吴萸素B(10)、二氢槲皮素(11)、曲霉三唑A(12)、反式油酸甲酯(13)、油酸(14)、10-二十碳烯酸(15)、芥酸酰胺(16)、油酸酰胺(17)、microphyllose A(18)、inotodisaccharide(19),其中化合物7、9、10、12、13、15-19为首次在蔷薇属植物中分离,化合物1为首次在该种中分离。(2)抗炎测试结果显示,除化合物1以外,其余6个三萜类化合物均能显著抑制NO生成,化合物4、化合物5、化合物6的IC₅₀值分别为(6.76±1.02)、(11.36±0.39)、(11.53±2.08)μmol·L^-1,活性优于或接近阳性对照氨基胍盐酸盐。该研究丰富了金樱子果实的化学成分,明确了三萜类为其主要抗炎活性成分,为其抗炎活性的物质基础及进一步开发与利用提供了科学依据。

Abstract:

To investigate the constituents of Rosa laevigata fruits and their anti-inflammatory activities, the ethyl acetate fraction of its ethanol extract was separated by silica gel column chromatography and semi-preparative HPLC. The isolated compounds were characterized by MS and NMR. Selected triterpenoids were tested for anti-inflammatory activities by measuring nitrix oxide(NO)production inhibition in lipopolysaccharide(LPS)-stimulated RAW264.7 macrophages. The results were as follows:(1)Nineteen compounds were isolated and identified from the ethyl acetate fraction, they were 2α,3α,19α-trihydroxy-28-norurs-12-ene(1), euscaphic acid(2), 1α,2β,3β,19α-tetrahydroxyurs-12-en-28-oic acid(3), 2α,3α,19α,23-tetraydroxyurs-12-en-28-oic acid(4), 2α,3β,19α,23-tetrahydroxyurs-12-en-28-oic acid(5), niga-ichigoside F1(6), hyptaic acid B(7), tiliroside(8), anemarrhenoside B(9), evofolin B(10), taxifolin(11), aspergillus triazolate A(12), methyl elaidate(13), oleic acid(14), 10-eicosenoic acid(15), erucylamide(16), 9(Z)-octadecenamide(17), microphyllose A(18), inotodisaccharide(19). Among them, compounds 7, 9, 10, 12, 13, 15-19 represented the first occurrence in the genus Rosa, and Compound 1 was reported for the first time from Rosa laevigata.(2)Anti-inflammatory activity tests showed that all tested triterpenoids except Compound 1 significantly inhibited NO production. Compounds 4, 5 and 6 exhibited IC₅₀ values of(6.76±1.02),(11.36±0.39)and(11.53±2.08)μmol·L^-1, respectively, with activities superior to or comparable to the positive control aminoquanidine hydrochloride. This study enriches the chemical constituents of R. laevigata fruit, identifies triterpenoids as its primary anti-inflammatory active components, and provides a scientific basis for the material foundation of its anti-inflammatory activity and further development and utilization.