Prenylated (iso)flavonoids as antifungal agents against the food spoiler Zygosaccharomycesparabailii. (February 2022)

• Record Type: Journal Article
• Authors: Kalli, Sylvia; Araya-Cloutier, Carla; Chapman, John; Sanders, Jan-Willem; Vincken, Jean-Paul
• Is Part Of: Food control. Volume 132(2022)
• Publication Date: 2022-02
• Subjects: Prenylated isoflavonoid -- Zygosaccharomyces parabailii -- Natural antifungal -- Membrane permeabilization -- Transmission electron microscopy; Food -- Quality -- Periodicals; Food -- Analysis -- Periodicals; Food handling -- Periodicals; Food industry and trade -- Quality control -- Periodicals; Aliments -- Industrie et commerce -- Qualité -- Contrôle -- Périodiques; Aliments -- Qualité -- Périodiques; Aliments -- Analyse -- Périodiques; Hygiène alimentaire -- Périodiques; Food -- Analysis; Food handling; Food -- Quality; Periodicals; Electronic journals; 664.07
• DOI: 10.1016/j.foodcont.2021.108434
• Languages: English
• ISSNs: 0956-7135

Abstract

Abstract: Species belonging to the Zygosaccharomyces bailii sensu lato clade are some of the most troublesome spoilage yeasts of acidic food products, primarily due to their resistance towards synthetic food preservatives, like weak organic acids. Therefore alternative, powerful and more natural antifungal agents are needed. Herein, prenylated isoflavonoids, present mainly in the Leguminosae family, were investigated for their antifungal properties (including potency and mode of action) against a Z. bailii food isolate, its interspecies hybrid, Z. parabailii . The mono-prenylated isoflavonoids, wighteone and glabridin were the most active, with minimum fungicidal concentrations (MFC) of 12.5 μg/mL (37 μM) and 25 μg/mL (77 μM), respectively, at pH 4.0, rendering them over 20 times (on weight basis) more potent than sorbic acid (MFC 550 μg/mL, 4.5 mM). The two active mono-prenylated isoflavonoids induced killing within 15 min, suggesting potential membrane activity. Membrane permeabilization by these molecules was confirmed by propidium iodide uptake and TEM imaging. Membrane permeabilization was accompanied with leakage of intracellular material. Molecular properties such as the electrostatic energy potential and the hydrophobic integy moment were correlated to activity through a binary classification quantitative structure-activity relationship (QSAR) model. Altogether, mono-prenylated isoflavonoids can serve as highly potent, novel and natural antifungal against Z. parabailii acting by severely compromising the membrane integrity. Highlights: Mono- are better than di-prenylated isoflavonoids as anti- Z.parabaili agents. Mono-prenylated wighteone kills Z. parabailii at 12.5 μg/mL at pH 4.0. Wighteone and glabridin kill Z. parabailii within 15 min at pH 4.0. Wighteone and glabridin deform the membrane of Z. parabailii, as evidenced by TEM.