TY - JOUR
T1 - Antibacterial prenylated stilbenoids from peanut (Arachis hypogaea)
AU - de Bruijn, Wouter J.C.
AU - Araya-Cloutier, Carla
AU - Bijlsma, Judith
AU - de Swart, Anne
AU - Sanders, Mark G.
AU - de Waard, Pieter
AU - Gruppen, Harry
AU - Vincken, Jean Paul
PY - 2018/12
Y1 - 2018/12
N2 - 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.
AB - 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.
KW - Antimicrobial
KW - Leguminosae
KW - Natural product
KW - Prenylation
KW - Secondary metabolite
KW - Stilbene
U2 - 10.1016/j.phytol.2018.09.004
DO - 10.1016/j.phytol.2018.09.004
M3 - Article
AN - SCOPUS:85052965868
SN - 1874-3900
VL - 28
SP - 13
EP - 18
JO - Phytochemistry Letters
JF - Phytochemistry Letters
ER -