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Synthesis of N-hydroxycinnamoyl amino acid ester analogues and their free radical scavenging and antioxidative activities

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Abstract

Hydroxycinnamic acids have a variety of biological activities, including antioxidant activity. To find more active antioxidants with hydroxycinnamoyl moiety, we synthesized a series of N-hydroxycinnamoyl amino acid esters and evaluated their antioxidative activities by 2,2-diphenyl-1-picryl hydrazyl (DPPH) radical scavenging and human red blood cells (RBCs) haemolysis methods. It was found that N-caffeoyl amides exhibited the highest DPPH-scavenging activities, whereas N-feruloyl amides demonstrated the highest antihaemolysis activities among the three different hydroxycinnamamides (caffeoyl, feruloyl, and p-coumaroyl), and that hydroxycinnamoyl amides were more effective than their corresponding free acid and ester compounds in both DPPH and RBC haemolysis tests.

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Acknowledgments

This work was supported by the National Natural Science Foundation of China (Grant NO. 20702016).

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Correspondence to Hong Jiang.

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Wei, QY., Jiang, H., Zhang, JX. et al. Synthesis of N-hydroxycinnamoyl amino acid ester analogues and their free radical scavenging and antioxidative activities. Med Chem Res 21, 1905–1911 (2012). https://doi.org/10.1007/s00044-011-9713-2

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  • DOI: https://doi.org/10.1007/s00044-011-9713-2

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