Synthesis and Evaluation of Antimicrobial and Antibiofilm Properties of A-Type Procyanidin Analogues against Resistant Bacteria in Food

Journal of Agricultural and Food Chemistry
Alfonso Alejo-ArmijoElena Ortega-Morente

Abstract

Natural A-type procyanidins have shown very interesting biological activities, such as their proven antiadherence properties against pathogenic bacteria. In order to find the structural features responsible for their activities, we describe herein the design and synthesis of six A-type procyanidin analogues and the evaluation of their antimicrobial and antibiofilm properties against 12 resistant bacteria, both Gram positive and Gram negative, isolated from organic foods. The natural A-type procyanidin A-2, which had known antiadherence activity, was also tested as a reference compound for the comparative studies. Within the series, analogue 4, which had a NO2group on ring A, showed the highest antimicrobial activity (MIC of 10 μg/mL) and was one of the best molecules at preventing biofilm formation (up to 40% decreases at 100 μg/mL) and disrupting preformed biofilms (up to 40% reductions at 0.1 μg/mL). Structure-activity relationships are also analyzed.

References

Mar 7, 2002·Journal of Agricultural and Food Chemistry·Adrian J CharltonMichael P Williamson
Jun 1, 2002·Applied and Environmental Microbiology·D DjordjevicL A McLandsborough
Apr 27, 2004·Oral Microbiology and Immunology·A YamanakaK Okuda
May 28, 2004·The Journal of Antimicrobial Chemotherapy·Doron SteinbergErvin I Weiss
Jun 27, 2007·Antimicrobial Agents and Chemotherapy·Analy S MeloBeth A Arthington-Skaggs
May 29, 2006·Tetrahedron·Carolyn Selenski, Thomas R R Pettus
Feb 19, 2009·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·George A KrausAaron Kempema
Apr 20, 2010·Biochemical and Biophysical Research Communications·Lilian S AmerMonique L van Hoek
Feb 1, 2011·International Journal of Food Microbiology·Brigitte Carpentier, Olivier Cerf
Mar 8, 2013·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Giuseppe CalogeroFernando Pina
Dec 17, 2014·BMC Complementary and Alternative Medicine·Robert K UlreyMonique L van Hoek
Dec 12, 2017·European Journal of Medicinal Chemistry·Aurelia Magdalena PisoschiEndre Mathe

❮ Previous
Next ❯

Citations

Mar 7, 2020·Organic & Biomolecular Chemistry·Ádám SzappanosTibor Kurtán
Jul 8, 2020·Journal of Agricultural and Food Chemistry·Alfonso Alejo-ArmijoJoaquı N Altarejos
Jan 22, 2020·Organic Letters·Luqiong HuoHaibo Tan

❮ Previous
Next ❯

Related Concepts

Related Feeds

Antifungals

An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.

Biofilms

Biofilms are adherent bacterial communities embedded in a polymer matrix and can cause persistent human infections that are highly resistant to antibiotics. Discover the latest research on Biofilms here.

Biofilm & Infectious Disease

Biofilm formation is a key virulence factor for a wide range of microorganisms that cause chronic infections.Here is the latest research on biofilm and infectious diseases.

Antifungals (ASM)

An antifungal, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis, cryptococcal meningitis, and others. Discover the latest research on antifungals here.