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[摘要]
目的 研究波罗蜜Artocarpus heterophyllus根的化学成分及其生物活性。方法 采用HP-20大孔吸附树脂、sephadex LH-20凝胶等柱色谱以及制备高效液相技术进行化学成分分离,采用NMR和ESI-MS等光谱方法进行化合物结构鉴定;采用脂多糖(lipopolysaccharide,LPS)诱导RAW264.7细胞释放NO的细胞模型评价所分离化合物的抗炎活性。结果 分离得到6个异戊烯基黄酮衍生物,其结构分别鉴定为2S-5,7-二羟基-2-(2-羟基-4,6-二甲氧基苯基)-6-(3-甲基丁-2-烯-1-基)色原-4-酮(1)、heteroflavanone C(2)、kuwanon C(3)、artoindonesianin A-2(4)、artoindonesianin S(5)、norartocarpin(6)。化合物1、3、4能不同程度地抑制LPS诱导的RAW264.7细胞释放NO,其半数抑制浓度(median inhibition concentration,IC50)分别为(9.0±1.2)、(19.4±3.5)、(24.6±5.7)mmol/L,而化合物2、5、6则无明显的活性。结论 化合物1为新化合物,命名为波罗蜜黄烷酮D;化合物3~5为首次从波罗蜜属植物中分离得到,化合物6为首次从波罗蜜中分离得到。化合物1、3、4具有作为抗炎药物开发的潜在价值。
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[Abstract]
Objective To investige the chemical constituents from the roots of Artocarpus heterophyllus and their bioactivities. Methods HP-20 macroporous adsorption resin, Sephadex LH-20 gel column chromatography and preparative high performance liquid chromatography were used to separate the chemical constituents. The structures of all isolates were elucidated by spectroscopic methods, including NMR and HR-ESI-MS. The anti-inflammatory activity of all isolates was evaluated by using a cell model in which NO was produced by LPS-stimulated RAW264.7 cells. Results Six prenylated flavonoid derivatives were isolated and their structures were identified as 2S-5,7-dihydroxy-2-(2-hydroxy-4,6-dimethoxyphenyl)-6-(3-methylbut-2-en-1-yl) chroman-4- one (1), heteroflavanone C (2), kuwanon C (3), artoindonesianin A-2 (4), artoindonesianin S (5), and norartocarpin (6). Compounds 1, 3 and 4 inhibited the release of NO from LPS-induced RAW264.7 cells to varying degrees with the IC50 values of (9.0 ± 1.2), (19.4 ± 3.5) and (24.6 ± 5.7) µmol/L, respectively. In contrast, compounds 2, 5 and 6 showed no obvious activity against the NO production in LPS-stimulated RAW264.7 cells. Conclusion Compound 1 named as heteroflavanone D is a new structure. It is the first report of the occurrence of compounds 3—5 in the genus Artocarpus, and compound 6 is isolated from A. heterophyllus for the first time. Compounds 1, 3 and 4 have potential value as anti-inflammatory drugs.
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[基金项目]
江西中医药大学校级科技创新团队发展计划(CXTD22002);江西省教育厅科学技术研究项目(GJJ211243);江西省中医药管理局科技计划(2020A0355)