Natural A-type procyanidins have shown very interesting biological activities, such as their proven antiadherence properties against pathogenic bacteria. In order to find the structural features responsible for their activities, we describe herein the design and synthesis of six A-type procyanidin analogues and the evaluation of their antimicrobial and antibiofilm properties against 12 resistant bacteria, both Gram positive and Gram negative, isolated from organic foods. The natural A-type procyanidin A-2, which had known antiadherence activity, was also tested as a reference compound for the comparative studies. Within the series, analogue 4, which had a NO group on ring A, showed the highest antimicrobial activity (MIC of 10 μg/mL) and was one of the best molecules at preventing biofilm formation (up to 40% decreases at 100 μg/mL) and disrupting preformed biofilms (up to 40% reductions at 0.1 μg/mL). Structure-activity relationships are also analyzed.

Summary This study aimed to evaluate the antimicrobial and antibiofilm activities of two procyanidins isolated from an ethyl acetate extract of laurel wood against a selection of foodborne pathogens. The analysis of the extract by HPLC–DAD/ESI–MS allowed us to detect the presence of two procyanidins, which were selectively isolated and identified by chromatographic and spectroscopic means as cinnamtannin B‐1 (1) and procyanidin B‐2 (2). Procyanidins 1 and 2 exhibited two biological activities: inhibition of bacterial growth at high concentrations and prevention of biofilm formation at lower concentrations. Synergistic effect was also detected when both compounds were tested in combination against Listeria monocytogenes. Significant effects were also detected on disruption of preformed biofilm. The ability of procyanidins to inhibit microbial growth and biofilm formation and to synergistically work with each other may stimulate a market as natural food preservatives, and/or natural sanitisers for processing equipment where foodborne pathogens reside.

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Chlorhexidine (CH) and quaternary ammonium compounds (QAC), such as cetrimide (CE), are widely used as disinfectants because of their broad antimicrobial spectrum. However, their frequent use for disinfection in different settings may promote bacterial drug resistance against both biocides and clinically relevant antibiotics. This study analyzes the effects of stepwise exposure to cetrimide (CE) and chlorhexidine (CH) of bacteria from organic foods and previously classified as biocide-sensitive. Gradual exposure of these strains to biocides resulted in mainly transient decreased antimicrobial susceptibility to other antibiotics and to biocides. Biocide-adapted bacteria also exhibit alterations in physiological characteristics, mainly decreased heat tolerance, or gastric acid tolerance in CE-adapted strains, while bile resistance does not seem to be influenced by biocide adaptation. Results from this study suggest that changes in membrane fluidity may be the main mechanism responsible for the acquisition of stable tolerance to biocides.

BACKGROUND Heavy metal pollution may act as persistent selective pressure that favors the spread of antimicrobial resistance in natural environments. The aim of this study was to isolate and identify metal‐tolerant bacteria from soils in olive tree fields routinely treated with copper‐derived compounds and to evaluate the tolerance of bacterial strains to other metals and their resistance to clinically relevant antibiotics. RESULTS Five hundred and ninety‐five bacterial isolates from 45 olive tree agricultural fields were studied. Minimum inhibitory concentrations (MICs) ≥ 16 mmol L−1 were detected for copper (57% of isolates), zinc (37%) and lead (62%), while only 3% had MICs ≥ 12 mmol L−1 for nickel. Ninety‐six metal‐tolerant strains were selected for identification and antibiotic resistance determination. Most isolates belonged to the genera Pseudomonas (37%), Bacillus (23%) and Chryseobacterium (20%), while 6% were identified as Variovorax, 4% as Stenotrophomonas and 2% as Serratia or Burkholderia. Highest copper tolerance was detected among Pseudomonas. Over 75% of the strains with high copper tolerance were also resistant to vancomycin, 50% to ampicillin and 40% to erythromycin or trimethoprim/sulfamethoxazole. CONCLUSION Bacteria from olive soils are tolerant to metals, mainly copper, but also zinc and lead, as well as resistant to clinically important antibiotics, which could be a troublesome issue in clinical settings. © 2019 Society of Chemical Industry