杓唇石斛素类似物的合成及其抗炎活性
Synthesis and biological evaluation of moscatilin analogs as anti-inflammatory agents
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摘要: 以丁香醛（1）为原料，通过乙酰化保护羟基、醛基还原、氯代、与三苯基膦反应合成膦叶立德中间体（5），并在此基础上通过Wittig反应、脱乙酰基和双键还原反应，合成杓唇石斛素（moscatilin，MST）及其12个类似物（MST-1 ~ MST-12），结构经1H NMR、13C NMR和ESI-MS表征。采用细菌脂多糖诱导小鼠巨噬细胞RAW264.7炎症模型对目标化合物进行初步体外抗炎活性测试，结果表明：所有化合物均能不同程度抑制炎症因子NO的生成，其中MST-5的抗炎活性最强（IC50 = 0.428 μmol/L），MST-5有待进一步研究其抗炎机制。Abstract: Using syringaldehyde as raw material, the phosphine ylide intermediate was efficiently synthesized through acetylated hydroxyl protection, aldehyde group reduction, chlorination and reaction with triphenylphosphine. On this basis, moscatilin (MST) and its 12 analogs (MST-1-MST-12) were synthesized by wittig reaction, deacetylation and double bond reduction. All the structures were confirmed by 1H NMR, 13C NMR and ESI-MS. Bacterial lipopolysaccharide-induced mouse macrophage RAW264.7 inflammation model was used to conduct preliminary anti-inflammatory activity tests in vitro for the target compounds. Results showed that all compounds could inhibit the production of inflammatory factor NO, and that MST-5 exhibited the strongest anti-inflammatory activity (IC50= 0.428 μmol/L).Further exploration is expected for the study of the anti-inflammatory mechanism of MST-5.
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Keywords:
- moscatilin /
- bibenzyl /
- synthesis /
- anti-inflammatory activity
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