Rapid membrane permeabilization of Listeria monocytogenes and Escherichia coli induced by antibacterial prenylated phenolic compounds from legumes

Araya‐Cloutier, Carla; Vincken, Jean‐Paul; Ederen, Roan van; Besten, H.M.W. den; Gruppen, Harry

doi:10.1016/j.foodchem.2017.07.074

Cited by 50 publications

(41 citation statements)

References 33 publications

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“…These rearrangements will improve their intermolecular interactions with a potential target. The positive correlation of globularity with antibacterial activity of prenylated (iso)flavonoids is in accordance with our previous results 5 , where flatness of prenylated stilbenoids was associated with their relatively low antibacterial activity as opposed to the relatively good antibacterial activity of elbow-shaped prenylated (iso)flavonoids.…”

Section: Discussionsupporting

confidence: 92%

“…In the Fabaceae plant family, prenylated phenolic compounds have been identified as promising antimicrobials in extracts from elicited seedlings 4 , 5 . These phenolic compounds mainly belong to the flavonoid (2-phenyl benzopyrans), isoflavonoid (3-phenyl benzopyrans) and stilbenoid (1,2-diphenyl ethylene) classes.…”

Section: Introductionmentioning

confidence: 99%

“…We previously showed that intrinsic resistance in E . coli can be overcome by inhibiting the efflux pump systems 5 . Consequently, we here report the antibacterial activity of prenylated (iso)flavonoids against E .…”

Section: Introductionmentioning

confidence: 99%

“…The main goals of this study were (i) to develop a multiple linear regression model with high predictive capabilities for the activity of other prenylated (iso)flavonoids by using a QSAR approach, and (ii) to understand the mode of action of prenylated (iso)flavonoids against Gram positive and Gram negative bacteria by linking the QSAR findings to the proposed mode of action of prenylated (iso)flavonoids, i.e. disruption of membrane integrity 5 , 24 – 26 .…”

Section: Introductionmentioning

confidence: 99%

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QSAR-based molecular signatures of prenylated (iso)flavonoids underlying antimicrobial potency against and membrane-disruption in Gram positive and Gram negative bacteria

Araya‐Cloutier

Vincken

Schans

et al. 2018

Sci Rep

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Prenylated flavonoids and isoflavonoids are phytochemicals with remarkable antibacterial activity. In this study, 30 prenylated (iso)flavonoids were tested against Listeria monocytogenes and Escherichia coli (the latter in combination with an efflux pump inhibitor). Minimum inhibitory concentrations of the most active compounds ranged between 6.3–15.0 µg/mL. Quantitative structure-activity relationships (QSAR) analysis was performed and linear regression models were proposed with R2 between 0.77–0.80, average R2m between 0.70–0.75, Q2LOO between 0.66–0.69, and relatively low amount of descriptors. Shape descriptors (related to flexibility and globularity), together with hydrophilic/hydrophobic volume and surface area descriptors, were identified as important molecular characteristics related to activity. A 3D pharmacophore model explaining the effect of the prenyl position on the activity of compounds was developed for each bacterium. These models predicted active compounds with an accuracy of 71–88%. With regard to the mode of action, good antibacterial prenylated (iso)flavonoids with low relative hydrophobic surface area caused remarkable membrane permeabilization, whereas those with higher relative hydrophobic surface area did not. Based on the QSAR and membrane permeabilization studies, the mode of action of antibacterial prenylated (iso)flavonoids was putatively rationalized.

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Section: Discussionsupporting

confidence: 92%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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QSAR-based molecular signatures of prenylated (iso)flavonoids underlying antimicrobial potency against and membrane-disruption in Gram positive and Gram negative bacteria

Araya‐Cloutier

Vincken

Schans

et al. 2018

Sci Rep

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“…Previous studies have reported that some phenolic compounds derived from plants had effect on cytoplasmic membrane of bacterial cells and lost membrane integrity. 32,33,34 These results could be concluded that the C. sappan extract has the capacity to interrupt biofilm formation and cell membrane formation, thus can be used as an antimicrobial agent. …”

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confidence: 84%

High Antioxidant and Phenolic Contents Related to Antibacterial Activity against Gastrointestinal Pathogenic Bacteria of Some Thai Medicinal Plants

Phalanisong¹,

Vichitphan²,

Han³

et al. 2018

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Objective: Thai medicinal plants were used as the traditional medicines and as part of everyday plants diet. Plants contain a mixture of phytochemical and exhibit a lot of functional food and medicinal properties. This project aims to investigate the potential of selected Thai medicinal plants according to the properties of their antioxidant and antibacterial activities. Methods: The eighteen plants were extracted using maceration method with 95% ethanol. The antioxidant activity was evaluated by DPPH and FRAP assay. The total phenolic content was evaluated by Folin-Ciocalteu phenol reagent. The antibacterial activity was evaluated by agar disc diffusion method. The extract which exhibited high antioxidant and antibacterial activity was selected to observe morphological changes by the scanning electron microscope (SEM). Results: The extract of Caesalpinia sappan showed the highest activities on both antioxidant assayed by FRAP method and total phenolic contents, however, exhibited high antioxidant assayed by DPPH compared to Bauhinia strychnifolia extract. Moreover, the extract of C. sappan showed the excellent antibacterial activities against six pathogenic bacteria in Gastro-intestinal tract. The morphological change by SEM was selected for further investigation antibacterial activities of C. sappan extract. The results showed that the inhibitory effect to those bacterial strains could be caused by the disruption of the cell membrane and decrease biofilm formation after treatment with the extract. Conclusion: The ethanol extract of C. sappan exhibited strong antioxidant and antibacterial activities against the six pathogenic bacteria. This result suggested that C. sappan could be applied to use for medicinal purpose and functional products. Key words: Antioxidant activity, Antibacterial activity, Total phenolic content, Caesalpinia sappan, Scanning electron microscope. 11,12,13 Previous studies showed the possibility to use many Thai plants as antioxidants and antibacterial agents. Some Thai plant extracts such as Cassia siamea, Garcinia cowa, Limnophila aromatica, Polygonum odoratum, Dioscorea bulbifera, Syzygium cumini and Zingiber zerumbet which have been reported for their antioxidant activities, and these plants also exhibit antibacterial against some pathogenic bacteria. 14,15,16,17 However, there are many medicinal Thai plants which are not to be evaluated their antioxidant related to antibacterial activities from GI tract. Due to the abovementioned facts, this project aims to investigate the potential of Thai plants according to the properties of the plant extracts on their antioxidant and antibacterial activities including their effects on morphological changes of selected pathogenic bacteria in GI tract. This information will be used as guide line for development of medicinal products and functional ingredients for use in novel functional food products. Parichat MATERIALS AND METHODS Sample collectionEighteen plant samples were selected based on Thai traditional medicine and their health pro...

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Soaking Water Functional Properties

Serventi

Gao

Chang

et al. 2020

Upcycling Legume Water: From Wastewater to Food Ingredients

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Rapid membrane permeabilization of Listeria monocytogenes and Escherichia coli induced by antibacterial prenylated phenolic compounds from legumes

Cited by 50 publications

References 33 publications

QSAR-based molecular signatures of prenylated (iso)flavonoids underlying antimicrobial potency against and membrane-disruption in Gram positive and Gram negative bacteria

QSAR-based molecular signatures of prenylated (iso)flavonoids underlying antimicrobial potency against and membrane-disruption in Gram positive and Gram negative bacteria

High Antioxidant and Phenolic Contents Related to Antibacterial Activity against Gastrointestinal Pathogenic Bacteria of Some Thai Medicinal Plants

Soaking Water Functional Properties

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