Antibacterial prenylated stilbenoids from peanut (Arachis hypogaea)

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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.

LanguageEnglish
Pages13-18
JournalPhytochemistry Letters
Volume28
Early online date8 Sep 2018
DOIs
Publication statusPublished - Dec 2018

Fingerprint

stilbenoids
Arachis hypogaea
peanuts
Methicillin
Metabolites
Derivatives
chemical derivatives
Microbial Sensitivity Tests
Methicillin-Resistant Staphylococcus aureus
minimum inhibitory concentration
Stilbenes
Liquid chromatography
Fungi
Nuclear magnetic resonance spectroscopy
stilbenes
resveratrol
Liquid Chromatography
secondary metabolites
liquid chromatography
Inhibitory Concentration 50

Keywords

  • Antimicrobial
  • Leguminosae
  • Natural product
  • Prenylation
  • Secondary metabolite
  • Stilbene

Cite this

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title = "Antibacterial prenylated stilbenoids from peanut (Arachis hypogaea)",
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.",
keywords = "Antimicrobial, Leguminosae, Natural product, Prenylation, Secondary metabolite, Stilbene",
author = "{de Bruijn}, {Wouter J.C.} and Carla Araya-Cloutier and Judith Bijlsma and {de Swart}, Anne and Sanders, {Mark G.} and {de Waard}, Pieter and Harry Gruppen and Vincken, {Jean Paul}",
year = "2018",
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doi = "10.1016/j.phytol.2018.09.004",
language = "English",
volume = "28",
pages = "13--18",
journal = "Phytochemistry Letters",
issn = "1874-3900",
publisher = "Elsevier",

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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

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SP - 13

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JO - Phytochemistry Letters

T2 - Phytochemistry Letters

JF - Phytochemistry Letters

SN - 1874-3900

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