Structure-activity relationship and membrane-targeting mechanisms of shikimate-related metabolites against Gram-positive and Gram-negative bacteria

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ID: 331911
2026
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Abstract
AIMS: The rise of antibiotic-resistant bacteria has intensified the search for novel antimicrobials. In this context, shikimic acid is a versatile scaffold widely used as a precursor to bioactive compounds and drugs. This study screened the antimicrobial activity and underlying mechanism of 18 shikimate-related metabolites against Escherichia coli and Staphylococcus epidermidis. METHODS AND RESULTS: The antimicrobial activity of the metabolites was initially evaluated by determining their minimum inhibitory concentrations (MICs). Caffeic acid, p-coumaric acid, and α-methylhydrocinnamic acid exhibited the lowest MIC values and were selected for further evaluation of bacterial inactivation kinetics and effects on bacterial cell surface and membrane integrity. α-Methylhydrocinnamic acid showed rapid antibacterial effects with maximum reductions of 3.2 and 3.9 log CFU.mL-1 for E. coli and S. epidermidis, respectively. Caffeic acid and p-coumaric acid were less effective, particularly against E. coli, where antimicrobial activity plateaued over time. In E. coli, caffeic acid and p-coumaric acid increased surface hydrophilicity by 15% and 46%, respectively, whereas in S. epidermidis, p-coumaric acid and α-methylhydrocinnamic acid reduced hydrophilicity by 55% and 67%. Zeta potential measurements showed less negative surface charges in E. coli following treatment with p-coumaric acid and α-methylhydrocinnamic acid, whereas in S. epidermidis, α-methylhydrocinnamic acid increased surface charge. Additionally, α-methylhydrocinnamic acid caused pronounced membrane disruption, with bacterial cells with damaged membranes reaching 70% in E. coli and 90% in S. epidermidis, alongside a 54% increase in K⁺ leakage for E. coli. CONCLUSIONS: These findings highlight the potential of cinnamic acid derivatives, particularly α-methylhydrocinnamic acid, may have potential for further investigation as antibacterial compounds or as adjuncts to conventional antimicrobial strategies.
Reference Key
openalex_W7221088741 Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Ana Rita Pereira, Ana Cristina Afonso, Pedro Silva, Anabela de Sousa Borges, Jean-Christophe Cintrat, Manuel V. Simões
Journal Journal of applied microbiology
Year 2026
DOI
10.1093/jambio/lxag252
URL
https://doi.org/10.1093/jambio/lxag252
Keywords Keywords not found

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