3种香叶基取代黄烷酮的合成及抗肿瘤活性

doi:10.11944/j.issn.1000-0518.2017.10.160494

摘要/Abstract

摘要：

3种香叶基黄烷酮是从毛泡桐(Paulownia tomentosa)水果中分离出的3种具有相似结构的黄酮类化合物。我们以廉价的2,4,6-三羟基苯乙酮,羟基苯甲醛为原料经过取代、氯甲基甲基醚保护、羟醛缩合、分子内的麦克加成反应以及脱甲基甲基醚合成了3个香叶基取代黄烷酮。其结构经过核磁共振氢谱及碳谱(¹H NMR,¹³C NMR )和高分辨质谱(HRMS)等技术手段进行了表征,并采用四氮唑蓝(MTT)法测试了合成化合物对肺癌细胞A459的体外抗肿瘤活性。结果表明,所合成的化合物均具有一定的抗肺癌细胞活性,其中化合物2抗肺癌活性明显优于化合物1和3,其半数抑制浓度为25.6 μmol/L,为临床疾病的治疗和药物的研发提供了参考。

关键词: 毛泡桐, 香叶基黄酮, 黄烷酮, 全合成, 抗肿瘤活性

Abstract:

Three geranylated flavanones isolated from the bark of Paulownia tomentosa were synthesized from phloroacetophenone and substituted hydroxybenzaldehydes via substitution, protection of phenolic hydroxyl group, aldol condensation, cyclization and deprotection reactions. Their structures were confirmed by proton and carbon(¹H and ¹³C) nuclear magnetic resonance(NMR) and high resolution mass spectrometry(HRMS). The inhibition assay of these flavanones against A459 cell by methyl thiazolyl tetrazolium(MTT) protocol, indicates that compound 2 exihibits the highest activity with an half maximal inhibitory concentration(IC₅₀) value at 25.6 μmol/L. This study provides a suggestion for drug development based on geranylated flavanone scaffold.

Key words: Paulownia tomentosa, geranylated flavanones, flavanone, total synthesis, antitumor activity

马涛, 杨金会, 牛明杰, 叶子平, 李方辉. 3种香叶基取代黄烷酮的合成及抗肿瘤活性[J]. 应用化学, 2017, 34(10): 1140-1149.

MA Tao, YANG Jinhui, NIU Mingjie, YE Ziping, LI Fanghui. Total Synthesis and Antitumor Activity of Three 6-Geranylated Flavanones[J]. Chinese Journal of Applied Chemistry, 2017, 34(10): 1140-1149.

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