title: The position of prenylation of isoflavonoids and stilbenoids from legumes (Fabaceae) modulates the antimicrobial activity against Gram positive pathogens.
abstract: The legume plant family (Fabaceae) is a potential source of antimicrobial phytochemicals. Molecular diversity in phytochemicals of legume extracts was enhanced by germination and fungal elicitation of seven legume species, as established by RP-UHPLC-UV-MS. The relationship between phytochemical composition, including different types of skeletons and substitutions, and antibacterial properties of extracts was investigated. Extracts rich in prenylated isoflavonoids and stilbenoids showed potent antibacterial activity against Listeria monocytogenes and methicillin-resistant Staphylococcus aureus at concentrations between 0.05 and 0.1% (w/v). Prenylated phenolic compounds were significantly (p<0.01) correlated with the antibacterial properties of the extracts. Furthermore, the position of the prenyl group within the phenolic skeleton also influenced the antibacterial activity. Overall, prenylated phenolics from legume seedlings can serve multiple purposes, e.g. as phytoestrogens they can provide health benefits and as natural antimicrobials they offer preservation of foods.
authors.affiliation: Laboratory of Food Chemistry, Wageningen University, P.O. Box 17, 6700 AA Wageningen, The Netherlands. Electronic address: carla.arayacloutier@wur.nl.
authors.forename: Carla
authors.initials: C
authors.lastname: Araya-Cloutier
authors.affiliation: Laboratory of Food Microbiology, Wageningen University, Wageningen, The Netherlands. Electronic address: heidy.denbesten@wur.nl.
authors.forename: Heidy M W
authors.initials: HM
authors.lastname: den Besten
authors.affiliation: Laboratory of Food Chemistry, Wageningen University, P.O. Box 17, 6700 AA Wageningen, The Netherlands; Department of Chemistry Education, Universitas Pendidikan Indonesia, Setiabudi 229, Bandung 40154, Indonesia. Electronic address: siti.aisyah@upi.edu.
authors.forename: Siti
authors.initials: S
authors.lastname: Aisyah
authors.affiliation: Laboratory of Food Chemistry, Wageningen University, P.O. Box 17, 6700 AA Wageningen, The Netherlands. Electronic address: harry.gruppen@wur.nl.
authors.forename: Harry
authors.initials: H
authors.lastname: Gruppen
authors.affiliation: Laboratory of Food Chemistry, Wageningen University, P.O. Box 17, 6700 AA Wageningen, The Netherlands. Electronic address: jean-paul.vincken@wur.nl.
authors.forename: Jean-Paul
authors.initials: JP
authors.lastname: Vincken
mesh_terms: D000900:Anti-Bacterial Agents / Q000032:analysis / Q000737:chemistry*; D000890:Anti-Infective Agents / Q000032:analysis*; D007887:Fabaceae / Q000737:chemistry*; D007529:Isoflavones / Q000737:chemistry*; D064209:Phytochemicals / Q000032:analysis; D048789:Phytoestrogens / Q000032:analysis; D010936:Plant Extracts / Q000737:chemistry*; D054876:Prenylation; D013267:Stilbenes / Q000737:chemistry*
chemical_list: D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D007529:Isoflavones; D064209:Phytochemicals; D048789:Phytoestrogens; D010936:Plant Extracts; D013267:Stilbenes
keywords: Antimicrobial activity; Fabaceae; Fungal elicitation; Phytochemical; Prenylation; RP-UHPLC–UV–MS/MS