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Record number 541276
Title Antibacterial prenylated stilbenoids from peanut (Arachis hypogaea)
Author(s) Bruijn, Wouter J.C. de; Araya-Cloutier, Carla; Bijlsma, Judith; Swart, Anne de; Sanders, Mark G.; Waard, Pieter de; Gruppen, Harry; Vincken, Jean Paul
Source Phytochemistry letters 28 (2018). - ISSN 1874-3900 - p. 13 - 18.
DOI https://doi.org/10.1016/j.phytol.2018.09.004
Department(s) Food Chemistry Group
VLAG
BioNanoTechnology
Publication type Refereed Article in a scientific journal
Publication year 2018
Availibility Full text available from 2020-12-01
Keyword(s) Antimicrobial - Leguminosae - Natural product - Prenylation - Secondary metabolite - Stilbene
Abstract

Stilbenoids are a class of secondary metabolites with a stilbene backbone that can be produced by peanut (Arachis hypogaea) as defence metabolites. Six monomeric prenylated stilbenoids, including the compound arachidin-6 (4), were isolated from extracts of fungus-elicited peanuts (Arachis hypogaea) using preparative liquid chromatography. Their structures were confirmed by MSn, HRMS and NMR spectroscopy and their antibacterial activity was evaluated against methicillin-resistant Staphylococcus aureus (MRSA). Similarly to other phenolic compounds, prenylated derivatives of stilbenoids were more active than their non-prenylated precursors piceatannol, resveratrol, and pinosylvin. Chiricanine A (6), a chain-prenylated pinosylvin derivative, was the most potent compound tested, with a minimum inhibitory concentration (MIC) of 12.5 μg mL−1. Arachidin-6 (4), a ring-prenylated piceatannol derivative, had moderate potency (MIC 50–75 μg mL−1). In conclusion, prenylated stilbenoids represent a group of potential natural antibacterials which show promising activity against MRSA.

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