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Cinnamic acid/β-ionone hybrids: synthesis and in vitro anticancer activity evaluation

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Abstract

The hybrid approach, encompassing two pharmacophores in one molecular scaffold, has attracted much attention in medicinal chemistry. In this study, we synthesized a panel of hybrid molecules based on the natural active ingredients, β-ionone and 3,4,5-trimethoxycinnamic acid. The results exhibited that 3,4,5-trimethoxy-hybrid displayed the most excellent cytotoxicity against cancer cells, whereas, the electron effect of substituents plays no distinct effect on antiproliferative activity. The cytotoxicity of 3,4,5-trimethoxy-hybrid may be due to its cell cycle arrest and apoptosis-inducing activities, which may be relationship with the reactive oxygen species generation, redox imbalance, lipid peroxidation and the collapse of mitochondrial membrane potential induced by 3,4,5-trimethoxy-hybrid in A549 (human lung adenocarcinoma) cells. In conclusion, 3,4,5-trimethoxy-hybrid could induce cancer cell apoptosis through the reactive oxygen species generation.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (Grant No. 81901420, 31800292, 21675071), Shandong Provincial Natural Science Foundation (Grant No. ZR2018LH022).

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Authors and Affiliations

  1. School of Pharmaceutical Sciences, Liaocheng University, Liaocheng, 252059, Shandong, China

    Peng-Xiao Li, Wen-Wen Mu, Jie Yang, Ren-Min Liu & Guo-Yun Liu

  2. Shandong Center for Disease Control and Prevention, Jinan, Shandong, China

    Yan-Mo Li

  3. Qingdao Vland Biotech INC, 3 Chunyang Road, Qingdao, Shandong, China

    Ya-Lei Sun

  4. Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, 312000, China

    Yan Li

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  1. Peng-Xiao Li
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  2. Yan-Mo Li
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  5. Yan Li
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Correspondence to Jie Yang or Guo-Yun Liu.

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Li, PX., Li, YM., Mu, WW. et al. Cinnamic acid/β-ionone hybrids: synthesis and in vitro anticancer activity evaluation. Monatsh Chem 152, 863–870 (2021). https://doi.org/10.1007/s00706-021-02799-3

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  • DOI: https://doi.org/10.1007/s00706-021-02799-3

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