Antimicrobial activities of synthetic ferulic acid derivatives

Nakauchi, Michiyo; Ikemoto, Shigeaki; Yamanishi, Hisako; Ozaki, Yoshihiko; Tsuno, Takuo; Nomura, Eisaku; Hosoda, Asao; Taniguchi, Hiroya

doi:10.5891/jafps.28.183

Cited by 7 publications

(7 citation statements)

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“…Interestingly A. flavus UBA 294 was the microorganism with the lowest MIC value for ferulic acid (MIC = 161 µM) [65]. A similar pattern was noticed for C. albicans , one strain being reported as susceptible with an MIC value of 659 µM [81], whereas another report showed an MIC value higher than 10 mM [80]. Sinapic acid ( 8 ), which is the most substituted of the common naturally-occurring cinnamic acids, showed significant activity against S. aureus 209 and Streptococcus pyogenes 10535 (MIC = 558 µM) [77].…”

Section: Natural and Synthetic Cinnamic Acidsmentioning

confidence: 82%

“…Pseudomonas aeruginosa ATCC 10145 and E. coli CECT 434 were also susceptible to ferulic acid (MIC = 515 µM) [79]. In addition the strain A. niger ATCC 11394 showed a low MIC value (MIC = 322 µM) [65], however the MIC value against another strain of A. niger was found to be higher than 10 mM [80]. Interestingly A. flavus UBA 294 was the microorganism with the lowest MIC value for ferulic acid (MIC = 161 µM) [65].…”

Section: Natural and Synthetic Cinnamic Acidsmentioning

confidence: 99%

“…The esters of ferulic acid 68 – 77 have been evaluated against different bacteria and fungi, and comparatively they have lower growth inhibitory activity compared to cinnamate and 4-coumarate esters. The MIC values of the ferulate esters 68 – 77 ranged between 201 µM and >10 mM against C. albicans , and between <25 µM and 6.0 mM against S. aureus [80,81]. The most active ferulate ester was identified to be 4-chloro-3-methylphenyl ferulate ( 75 ) achieving MIC values of 201 µM against C. albicans and C. krusei , of 50 µM against E. faecalis , 812 µM against E. coli , 401 µM against K. pneumoniae , and <25 µM against S. aureus [81].…”

Section: Natural and Synthetic Cinnamic Esters And Amidesmentioning

confidence: 99%

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Natural Cinnamic Acids, Synthetic Derivatives and Hybrids with Antimicrobial Activity

2014

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Antimicrobial natural preparations involving cinnamon, storax and propolis have been long used topically for treating infections. Cinnamic acids and related molecules are partly responsible for the therapeutic effects observed in these preparations. Most of the cinnamic acids, their esters, amides, aldehydes and alcohols, show significant growth inhibition against one or several bacterial and fungal species. Of particular interest is the potent antitubercular activity observed for some of these cinnamic derivatives, which may be amenable as future drugs for treating tuberculosis. This review intends to summarize the literature data on the antimicrobial activity of the natural cinnamic acids and related derivatives. In addition, selected hybrids between cinnamic acids and biologically active scaffolds with antimicrobial activity were also included. A comprehensive literature search was performed collating the minimum inhibitory concentration (MIC) of each cinnamic acid or derivative against the reported microorganisms. The MIC data allows the relative comparison between series of molecules and the derivation of structure-activity relationships.

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Section: Natural and Synthetic Cinnamic Acidsmentioning

confidence: 82%

Section: Natural and Synthetic Cinnamic Acidsmentioning

confidence: 99%

Section: Natural and Synthetic Cinnamic Esters And Amidesmentioning

confidence: 99%

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Natural Cinnamic Acids, Synthetic Derivatives and Hybrids with Antimicrobial Activity

2014

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“…Yet, only a few studies have reported on this abundant cinnamic acid ability to protect against C. albicans , and those studies only targeted growth suppression. In one study, a minimum inhibitory concentration (MIC) value of 659 μM FA (Ergün, Çoban, Onurdag, & Banoglu, ) prevented C. albicans growth, whereas another report showed a MIC value greater than 10 mM (Nakauchi, Ikemoto, Yamanishi, & Ozaki, ). This difference in the inhibitory concentrations of the active molecule could be due to the different strains or media used.…”

Section: Resultsmentioning

confidence: 99%

Histone acetylation increases in response to ferulic, gallic, and sinapic acids acting synergistically in vitro to inhibit Candida albicans yeast‐to‐hyphae transition

Câmara

Shi

Pedersen

et al. 2018

Phytotherapy Research

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Novel treatments are needed to prevent candidiasis/candidemia infection due to the emergence of Candida species resistant to current antifungals. Considering the yeastto-hyphae switch is a critical factor to Candida albicans virulence, phenols common in plant sources have been reported to demonstrating their ability to prevent dimorphism. Therefore, phenols present in many agricultural waste stress (ferulic (FA) and gallic (GA) acid) were initially screened in isolation for their yeast-to-hyphae inhibitory properties at times 3, 6, and 24 hr. Both FA and GA inhibited 50% of hyphae formation inhibitory concentration (IC 50 ) but at a concentration of 8.0 ± 0.09 and 90.6 ± 1.05 mM, respectively, at 24 hr. However, the inhibitory effect of FA increased by 1.9-2.6 fold when combined with different GA concentrations. GA and FA values decreased even lower when sinapic acid (SA) was added as a third component. As evidenced by concave isobolograms and combination indexes less than 1, both GA:F A and GA:FA:SA combinations acted synergistically to inhibit 50% hyphae formation at 24 hr. Lastly, acetylation of histone H3 lysine 56 acetylation (H3K56) was higher in response to the triple phenolic cocktail (using the IC 50 24 hr inhibitory concentration level) comparable with the nontreated samples, indicating that the phenols inhibited hyphal growth in part by targeting H3K56 acetylation.

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“…Of these, a broad spectrum of antimicrobial activity of ferulic acid (FA) against bacteria and yeasts have been documented . Moreover, some recent results from our own group and others have shown that grafting alkyl chains with a carboxyl group of phenolic acids seems to be a viable option for modifying its hydrophilic–lipophilic balance, and these new molecules exhibited emulsifying properties and enhanced multifunctional properties, including antimicrobial activity , and antioxidation …”

Section: Introductionmentioning

confidence: 99%

Alkyl Ferulate Esters as Multifunctional Food Additives: Antibacterial Activity and Mode of Action against Escherichia coli in Vitro

Shi

Zhu

Shao

et al. 2018

J. Agric. Food Chem.

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This work aims to prepare ferulic acid alkyl esters (FAEs) through the lipase-catalyzed reaction between methyl ferulate and various fatty alcohols in deep eutectic solvents and ascertain their antibacterial activities and mechanisms. Screens of antibacterial effects of FAEs against Escherichia coli ATCC 25922 (E. coli) and Listeria monocytogenes ATCC 19115 (L. monocytogenes) revealed that hexyl ferulate (FAC6) exerted excellent bacteriostatic and bactericidal effects on E. coli and L. monocytogenes (minimum inhibitory concentration (MIC): 1.6 and 0.1 mM, minimum bactericidal concentration (MBC): 25.6 and 0.2 mM, respectively). The antibacterial mechanism of FAC6 against E. coli was systematically studied to facilitate its practical use as a food additive with multifunctionalities. The growth and time-kill curves implied the partial cell lysis and inhibition of the growth of E. coli caused by FAC6. The result related to propidium iodide uptake and cell constituents' leakage (K + , proteins, nucleotides, and β-galactosidase) implied that bacterial cytomembranes were substantially compromised by FAC6. Variations on morphology and cardiolipin microdomains and membrane hyperpolarization of cells visually verified that FAC6 induced cell elongation and destructed the cell membrane with cell wall perforation. SDS-PAGE analysis and alterations of fluorescence spectra of bacterial membrane proteins manifested that FAC6 caused significant changes in constitutions and conformation of membrane proteins. Furthermore, it also could bind to minor grooves of E. coli DNA to form complexes. Meanwhile, FAC6 exhibited antibiofilm formation activity. These findings indicated that that FAC6 has promising potential to be developed as a multifunctional food additive.

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Antimicrobial activities of synthetic ferulic acid derivatives

Cited by 7 publications

References 0 publications

Natural Cinnamic Acids, Synthetic Derivatives and Hybrids with Antimicrobial Activity

Natural Cinnamic Acids, Synthetic Derivatives and Hybrids with Antimicrobial Activity

Histone acetylation increases in response to ferulic, gallic, and sinapic acids acting synergistically in vitro to inhibit Candida albicans yeast‐to‐hyphae transition

Alkyl Ferulate Esters as Multifunctional Food Additives: Antibacterial Activity and Mode of Action against Escherichia coli in Vitro

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