Synthesis, antioxidant activity in vitro, and cytotoxicity of naringenin acylhydrazone derivatives

DONG Jia-li1,2 LIAO Yue-ting1,2 JIAO Bi-ning2 SU Xue-su1

(1.College of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715)
(2.Laboratory of Quality and Safety Risk Assessment for Citrus Products, Ministry of Agriculture and Rural Affairs, Citrus Research Institute, Chinese Academy of Agricultural Sciences (Citrus Research Institute of Southwest University), Chongqing 400712)
【Novelty】In this experiment, 13 naringin acylhydrazone derivatives were synthesized by microwave-assisted method, 12 of which were not reported in the literature. The antioxidant activities in vitro of the 13 derivatives were determined by three methods: ABTS, FRAP and DPPH methods. The antioxidant activities of the obtained derivatives were all stronger than those of naringenin, and the antioxidant activity of 8 derivatives is 3 to 6 times higher than that of naringenin, indicating that the 4-position carbonyl group of naringenin can effectively improve the antioxidant activity of the parent through the reactive introduction of the acyl hydrazone group. The results provide a theoretical basis for the later screening of antioxidant food additives and antioxidant drugs.

【Abstract】Naringenin has low bioavailability despite the strong antioxidant activity, thus limiting the application. In this article, 13 naringenin acylhydrazone derivatives were synthesized and 12 of them had not been reported. The in vitro antioxidant activity of 13 derivatives was determined by ABTS, FRAP, and DPPH methods. The results showed that the antioxidant activity of 13 compounds was stronger than that of naringenin, and the antioxidant activity of 8 derivatives was 3–6 times higher than that of naringenin. In the cytotoxicity test, cell survival rate > 90% suggested no inhibition of cells. In the concentration range of 0–25 mol/L, derivatives b, g, j, k, and l witnessed the survival rate of HEK293 cells > 90%. In addition, when the concentration of derivatives g, k, and l was 0–50 μmol/L, the survival rate of HEK293 cells was still more than 90%. Especially when the concentration of derivative j was as high as 100 μmol/L, the cell survival rate was still above 90%. The results lay a theoretical basis for the later screening of antioxidant food additives and antioxidant drugs.

【Keywords】 naringenin; acylhydrazone; antioxidant activity; cytotoxicity;


【Funds】 National Key Research and Development Project of China (2019YFC1605604-2) China Agriculture (Orange) Research System (CARS-26) National Agricultural Product Quality and Safety Risk Assessment Special Project (GJFP2019043)

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This Article



Vol 33, No. 04, Pages 535-542

April 2021


Article Outline



  • 1 Materials and methods
  • 2 Results and analysis
  • 3 Conclusions
  • References