Benzocaine as a precursor of promising derivatives: synthesis, reactions, and biological activity

Taha, Israa; Keshk, Eman M.; Khalil, A. M.; Fekri, Ahmed

doi:10.1007/s11696-021-01808-3

Cited by 4 publications

(1 citation statement)

References 214 publications

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“…Benzocaine (also known as ethyl p-amino benzoate, with the chemical formula C 9 H 11 NO 2 ) 17 is an S. chinensis -derived phenylpropanoid that exhibits low solubility in water but is readily soluble in organic solvents, such as alcohols, ethers, and chloroform 18 .It is widely used as a local anaesthetic, and exhibits clinical application in analgesia and antipruritic treatment of wounds, ulcers, burns, skin abrasions, and haemorrhoids 19 – 22 . It has antifungal, anti-inflammatory, and anticancer properties 23 , rendering it a widely used medicinal compound. Benzocaine gel has demonstrated efficacy in treating oral ulcers and toothaches; it also has antifungal activity against S. aureus 24 .…”

Section: Introductionmentioning

confidence: 99%

Inhibitory effect of benzocaine from Schisandra chinensis on Alternaria alternata

Long,

Zhao,

Zhang

et al. 2024

Sci Rep

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The clinical effects of Schisandra chinensis against human disease are well-documented; however, studies on its application in controlling plant pathogens are limited. Here, we investigated its inhibitory effect on the growth of Alternaria alternata, a fungus which causes significant post-harvest losses on apples, known as black spot disease. S. chinensis fruit extract exhibited strong inhibitory effects on the growth of A. alternata with an EC50 of 1882.00 mg/L. There were 157 compounds identified in the extract by high performance liquid chromatography-mass spectrometry, where benzocaine constituted 14.19% of the extract. Antifungal experiments showed that the inhibitory activity of benzocaine on A. alternata was 43.77-fold higher than the crude extract. The application of benzocaine before and after A. alternata inoculation on apples prevented the pathogen infection and led to mycelial distortion according to scanning electron microscopy. Transcriptome analysis revealed that there were 4226 genes differentially expressed between treated and untreated A. alternata-infected apples with benzocaine. Metabolomics analysis led to the identification of 155 metabolites. Correlation analysis between the transcriptome and metabolome revealed that benzocaine may inhibit A. alternata growth via the beta-alanine metabolic pathway. Overall, S. chinensis extract and benzocaine are environmentally friendly plant-based fungicides with potential to control A. alternata.

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