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

Jun. 2,2022
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Naringenin, as a dihydroflavonoid, possesses antibacterial, anti-tumor, and antioxidant activity. However, the poor lipid and water solubility of naringenin leads to the poor bioavailability. Therefore, naringenin modification has attracted the interest of a lot of scholars. The phenolic hydroxyl groups at positions 7 and 4′ and the carbonyl group at position 4 of naringenin are active. Thus, the structure of naringenin can be modified by chemical reactions to improve the water solubility and further the bioavailability. Hydrazides demonstrate strong antioxidant activity, antibacterial activity, and anti-cancer activity, but they are toxic due to the amino groups. Therefore, the modification of hydrazides to obtain acylhydrazones is an effective means to alleviate the toxicity of hydrazides.

Su Xue-su and his team from College of Chemistry and Chemical Engineering, Southwest University, based on the structure-activity relationship and modification of naringenin, added the hydrazide group at the position 4 to form an acylhydrazone, expecting to obtain naringenin derivatives with both biological activity and reduced toxicity of the hydrazide structure. 13 kinds of naringenin acylhydrazone derivatives were synthesized, 12 of them have not been reported in the literature. The antioxidant activity of 13 compounds is stronger than that of naringenin, and the antioxidant activity of 8 derivatives is 3 to 6 times higher than that of naringenin. The results provide a theoretical basis for the later screening of antioxidant food additives and antioxidant drugs.

The related research was completed by Dong Jia-li, Liao Yue-ting, Su Xue-su. Results are published in the 33rd volume, 4th issue of Natural Products Research and Development, 2021. The bilingual version has been launched.

Corresponding Author: DONG Jiali
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CNKI Press Officer: LI Jingjing YANG Na
Email: ljj6806@cnki.net yn6791@cnki.net

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