Structural requirements for the antimicrobial activity of carvacrol

Journal of Agricultural and Food Chemistry
Edwin J A VeldhuizenHenk P Haagsman

Abstract

Carvacrol is a component of several essential oils and has been shown to exert antimicrobial activity. The structural requirements for the activity of carvacrol were determined by comparison to structurally related (nonessential oil) compounds. Removal of the aliphatic ring substituents of carvacrol slightly decreased the antimicrobial activity. The effect of the hydroxyl group of carvacrol on activity could not be determined by simply comparing it to p-cymene, because this compound is immiscible with water; therefore, 2-amino-p-cymene, the amino analogue of carvacrol, which has a similar hydrophobicity and structural characteristics, was used. 2-Amino-p-cymene had similar membrane disruption and bacterial killing characteristics as carvacrol showing that, contrary to previous reports, the hydroxyl group of carvacrol itself is not essential for the antimicrobial activity. However, the observed 3-fold lower activity for 2-amino-p-cymene as compared to carvacrol indicates special features in the antimicrobial mode of action of carvacrol due to the hydroxyl group.

References

Jun 1, 1995·Microbiological Reviews·J SikkemaB Poolman
Mar 1, 1995·The Journal of Applied Bacteriology·C F Carson, T V Riley
Jun 1, 1994·The Journal of Applied Bacteriology·B J JuvenH Weisslowicz
Sep 28, 1999·Letters in Applied Microbiology·S CosentinoF Palmas
Oct 3, 1999·Applied and Environmental Microbiology·A UlteeE J Smid
Mar 29, 2000·Journal of Applied Microbiology·H J Dorman, S G Deans
May 29, 2000·Journal of Food Protection·A UlteeE J Smid
Apr 11, 2001·International Journal of Food Microbiology·A Ultee, E J Smid
Jan 8, 2005·Phytomedicine : International Journal of Phytotherapy and Phytopharmacology·A AllahverdiyevS Koltas
Feb 22, 2005·Oral Microbiology and Immunology·N ChamiA Remmal
Mar 18, 2005·Journal of Food Protection·Karla Rivera-CarrilesAurelio López-Malo
Jun 21, 2005·BMC Microbiology·Gabriella Kiskó, Sibel Roller
Sep 1, 1989·Journal of Food Protection·R S FaragG S A El-Baroty

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Citations

Sep 14, 2012·ACS Applied Materials & Interfaces·Simona MagginiRosa Di Maggio
Oct 7, 2010·British Poultry Science·R J WallaceK Teichmann
Mar 1, 2013·Critical Reviews in Microbiology·Wendy T LangeveldSara A Burt
Jun 11, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Stella W NowotarskaChen Situ
Mar 15, 2015·Journal of Oleo Science·Hamdy A Shaaban, Amr E Edris
Oct 6, 2012·Journal of Applied Microbiology·A Ait-OuazzouD García-Gonzalo
May 6, 2011·Phytotherapy Research : PTR·Rui-Hua DongZe-Yuan Liu
Jun 4, 2014·Journal of Food Science·Phakawat Tongnuanchan, Soottawat Benjakul
May 12, 2009·Journal of Medical Microbiology·Antonia NostroGiuseppe Bisignano
Oct 5, 2013·Journal of Enzyme Inhibition and Medicinal Chemistry·Reshma AlokamDharmarajan Sriram
Mar 29, 2013·Journal of Microencapsulation·Joyce Maria Gomes da CostaViviane Machado de Azevedo
Feb 1, 2015·Phytomedicine : International Journal of Phytotherapy and Phytopharmacology·Tahereh FalsafiBehzhad Hamedi
Jul 26, 2012·The Journal of Physical Chemistry. B·J KrupaM Wierzejewska
Apr 11, 2015·PloS One·Ivana CacciatoreLuigina Cellini
Nov 30, 2013·Pharmaceuticals·Filomena NazzaroVincenzo De Feo
Feb 10, 2018·Antimicrobial Resistance and Infection Control·Yi-Ming WangHong-Xia Ma
Aug 31, 2017·Critical Reviews in Food Science and Nutrition·Elien Van de VelKatleen Raes
Apr 15, 2018·Journal of Chemical Ecology·Joseph J KarchesyM P González-Hernández

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