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    Cinnamaldehydes: Synthesis, antibacterial evaluation, and the effect of molecular structure on antibacterial activity


    Doyle, Amanda A. and Krämer, Tobias and Kavanagh, Kevin and Stephens, John C. (2019) Cinnamaldehydes: Synthesis, antibacterial evaluation, and the effect of molecular structure on antibacterial activity. Results in Chemistry, 1 (100013). ISSN 2211-7156

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    Abstract

    trans-Cinnamaldehyde is a major component of Cinnamomum cassia and has been reported to give rise to antimicrobial properties in cinnamon spice. In order to better understand the relationship between the structure of trans-cinnamaldehyde and its antimicrobial role, fifteen structurally different trans-cinnamaldehyde derivatives were selected for study based on their predicted electrophilicities. Both synthesized and commercial transcinnamaldehyde derivatives were evaluated for their antibacterial activity, with modest mM activity levels found against both E. coli and S. aureus. An initial mechanism of action study, suggesting that the electrophilicity of the trans-cinnamaldehydes affects the antibacterial activity, was conducted as well as an exploration of their ability to alter bacterial cell wall integrity. In addition, in vivo toxicity levels were determined using the larvae of the greater wax moth, Galleria mellonella, with all derivatives tested showing low toxicity.

    Item Type: Article
    Additional Information: Cite as: Amanda A. Doyle, Tobias Krämer, Kevin Kavanagh, John C. Stephens, Cinnamaldehydes: Synthesis, antibacterial evaluation, and the effect of molecular structure on antibacterial activity, Results in Chemistry, Volume 1, 2019, 100013, ISSN 2211-7156, https://doi.org/10.1016/j.rechem.2019.100013.
    Keywords: Cinnamaldehyde; Cinnamaldehyde derivatives; Wittig, antibacterial; Electrophilicity;
    Academic Unit: Faculty of Science and Engineering > Biology
    Faculty of Science and Engineering > Chemistry
    Faculty of Science and Engineering > Research Institutes > Hamilton Institute
    Faculty of Science and Engineering > Research Institutes > Human Health Institute
    University Library
    Item ID: 13982
    Identification Number: https://doi.org/10.1016/j.rechem.2019.100013
    Depositing User: Tobias Krämer
    Date Deposited: 09 Feb 2021 17:14
    Journal or Publication Title: Results in Chemistry
    Publisher: Elsevier
    Refereed: Yes
    URI:

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