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

Research output: Contribution to journalArticleAcademicpeer-review

8 Citations (Scopus)

Abstract

Prenylated phenolics from the Fabaceae are promising lead compounds for new antibacterials. Pools enriched in prenylated phenolics were made from lupine, peanut and soybean seedlings. One pool was rich in chain prenylated isoflavones (cIsf), one in chain prenylated stilbenoids (cSti), one in chain prenylated (cPta) and one in ring-closed prenylated pterocarpans (rPta), as characterized by RP-UHPLC-UV-MS. Antibacterial activity of the pools and membrane permeabilization was investigated. Pools showed high antibacterial activity against Listeria monocytogenes: cIsf pool had a minimum inhibitory concentration of 10 µg/ml prenylated compounds, followed by cPta pool (25 µg/ml) and cSti pool (35 µg/ml). Activity against E. coli was found only when the pools were co-administered with an efflux pump inhibitor. The pool enriched in chain prenylated isoflavones permeabilized the bacterial membrane within minutes of exposure, whereas ampicillin did not. Bent conformation and chain prenylation, were molecular features of main prenylated phenolics found in pools with high antibacterial activity.
LanguageEnglish
Pages147-155
JournalFood Chemistry
Volume240
DOIs
Publication statusPublished - 2018

Fingerprint

Listeria
Isoflavones
Listeria monocytogenes
isoflavones
stilbenoids
Fabaceae
Escherichia coli
phenolic compounds
legumes
Membranes
Pterocarpans
Lupinus
Lead compounds
Prenylation
Microbial Sensitivity Tests
Ampicillin
ampicillin
minimum inhibitory concentration
Seedlings
Soybeans

Keywords

  • Antibacterial activity
  • Fabaceae
  • Membrane permeabilization
  • Prenylated phenolics
  • Structure-activity relationships

Cite this

@article{a23194fec0d74931a23bc2e42ea37a96,
title = "Rapid membrane permeabilization of Listeria monocytogenes and Escherichia coli induced by antibacterial prenylated phenolic compounds from legumes",
abstract = "Prenylated phenolics from the Fabaceae are promising lead compounds for new antibacterials. Pools enriched in prenylated phenolics were made from lupine, peanut and soybean seedlings. One pool was rich in chain prenylated isoflavones (cIsf), one in chain prenylated stilbenoids (cSti), one in chain prenylated (cPta) and one in ring-closed prenylated pterocarpans (rPta), as characterized by RP-UHPLC-UV-MS. Antibacterial activity of the pools and membrane permeabilization was investigated. Pools showed high antibacterial activity against Listeria monocytogenes: cIsf pool had a minimum inhibitory concentration of 10 µg/ml prenylated compounds, followed by cPta pool (25 µg/ml) and cSti pool (35 µg/ml). Activity against E. coli was found only when the pools were co-administered with an efflux pump inhibitor. The pool enriched in chain prenylated isoflavones permeabilized the bacterial membrane within minutes of exposure, whereas ampicillin did not. Bent conformation and chain prenylation, were molecular features of main prenylated phenolics found in pools with high antibacterial activity.",
keywords = "Antibacterial activity, Fabaceae, Membrane permeabilization, Prenylated phenolics, Structure-activity relationships",
author = "Carla Araya-Cloutier and Vincken, {Jean Paul} and {van Ederen}, Roan and {den Besten}, {Heidy M.W.} and Harry Gruppen",
year = "2018",
doi = "10.1016/j.foodchem.2017.07.074",
language = "English",
volume = "240",
pages = "147--155",
journal = "Food Chemistry",
issn = "0308-8146",
publisher = "Elsevier",

}

TY - JOUR

T1 - Rapid membrane permeabilization of Listeria monocytogenes and Escherichia coli induced by antibacterial prenylated phenolic compounds from legumes

AU - Araya-Cloutier, Carla

AU - Vincken, Jean Paul

AU - van Ederen, Roan

AU - den Besten, Heidy M.W.

AU - Gruppen, Harry

PY - 2018

Y1 - 2018

N2 - Prenylated phenolics from the Fabaceae are promising lead compounds for new antibacterials. Pools enriched in prenylated phenolics were made from lupine, peanut and soybean seedlings. One pool was rich in chain prenylated isoflavones (cIsf), one in chain prenylated stilbenoids (cSti), one in chain prenylated (cPta) and one in ring-closed prenylated pterocarpans (rPta), as characterized by RP-UHPLC-UV-MS. Antibacterial activity of the pools and membrane permeabilization was investigated. Pools showed high antibacterial activity against Listeria monocytogenes: cIsf pool had a minimum inhibitory concentration of 10 µg/ml prenylated compounds, followed by cPta pool (25 µg/ml) and cSti pool (35 µg/ml). Activity against E. coli was found only when the pools were co-administered with an efflux pump inhibitor. The pool enriched in chain prenylated isoflavones permeabilized the bacterial membrane within minutes of exposure, whereas ampicillin did not. Bent conformation and chain prenylation, were molecular features of main prenylated phenolics found in pools with high antibacterial activity.

AB - Prenylated phenolics from the Fabaceae are promising lead compounds for new antibacterials. Pools enriched in prenylated phenolics were made from lupine, peanut and soybean seedlings. One pool was rich in chain prenylated isoflavones (cIsf), one in chain prenylated stilbenoids (cSti), one in chain prenylated (cPta) and one in ring-closed prenylated pterocarpans (rPta), as characterized by RP-UHPLC-UV-MS. Antibacterial activity of the pools and membrane permeabilization was investigated. Pools showed high antibacterial activity against Listeria monocytogenes: cIsf pool had a minimum inhibitory concentration of 10 µg/ml prenylated compounds, followed by cPta pool (25 µg/ml) and cSti pool (35 µg/ml). Activity against E. coli was found only when the pools were co-administered with an efflux pump inhibitor. The pool enriched in chain prenylated isoflavones permeabilized the bacterial membrane within minutes of exposure, whereas ampicillin did not. Bent conformation and chain prenylation, were molecular features of main prenylated phenolics found in pools with high antibacterial activity.

KW - Antibacterial activity

KW - Fabaceae

KW - Membrane permeabilization

KW - Prenylated phenolics

KW - Structure-activity relationships

U2 - 10.1016/j.foodchem.2017.07.074

DO - 10.1016/j.foodchem.2017.07.074

M3 - Article

VL - 240

SP - 147

EP - 155

JO - Food Chemistry

T2 - Food Chemistry

JF - Food Chemistry

SN - 0308-8146

ER -