Unlabelled: The diverse and large-scale application of disinfectants posed potential health risks and caused ecological damage during the 2019-nCoV pandemic, thereby increasing the demands for the development of disinfectants based on natural products, with low health risks and low aquatic toxicity. In the present study, a few natural naphthoquinones and their derivatives bearing the 1,4-naphthoquinone skeleton were synthesized, and their antibacterial activity against selected bacterial strains was evaluated. antibacterial activities of the compounds were investigated against and Under the minimum inhibitory concentration (MIC) of ⩽ 0.125 µmol/L for juglone (1a), 5,8-dimethoxy-1,4-naphthoquinone (1f), and 7-methyl-5-acetoxy-1,4-naphthoquinone (3c), a strong antibacterial activity against was observed. All 1,4-naphthoquinone derivatives exhibited a strong antibacterial activity, with MIC values ranging between 15.625 and 500 µmol/L and EC values ranging between 10.56 and 248.42 µmol/L. Most of the synthesized compounds exhibited strong antibacterial activities against Among these compounds, juglone (1a) showed the strongest antibacterial activity. The results from mechanistic investigations indicated that juglone, a natural naphthoquinone, caused cell death by inducing reactive oxygen species production in bacterial cells, leading to DNA damage. In addition, juglone could reduce the self-repair ability of bacterial DNA by inhibiting RecA expression. In addition to having a potent antibacterial activity, juglone exhibited low cytotoxicity in cell-based investigations. In conclusion, juglone is a strong antibacterial agent with low toxicity, indicating that its application as a bactericidal agent may be associated with low health risks and aquatic toxicity.
Electronic Supplementary Material: Supplementary material is available in the online version of this article at 10.1007/s11783-023-1631-2 and is accessible for authorized users.
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