Structural requirements for the antimicrobial activity of carvacrol

Journal of Agricultural and Food Chemistry

Volumn 54, Issue 5, 2006, Pages 1874-1879

  Veldhuizen, Edwin J A ^a,b   Tjeerdsma Van Bokhoven, Johanna L M ^a,b   Zweijtzer, Cindy ^a   Burt, Sara A ^a   Haagsman, Henk P ^a,b  

^a UTRECHT UNIVERSITY   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

Antimicrobial activity; Carvacrol; Essential oil

Indexed keywords

2 AMINO P CYMENE; 2-AMINO-P-CYMENE; ANTIINFECTIVE AGENT; CARVACROL; TERPENE;

ARTICLE; CHEMISTRY; COMPARATIVE STUDY; DRUG EFFECT; ESCHERICHIA COLI; HYDROXYLATION; SOLUBILITY; STAPHYLOCOCCUS AUREUS; STRUCTURE ACTIVITY RELATION;

ANTI-INFECTIVE AGENTS; ESCHERICHIA COLI; HYDROXYLATION; MONOTERPENES; SOLUBILITY; STAPHYLOCOCCUS AUREUS; STRUCTURE-ACTIVITY RELATIONSHIP;

BACTERIA (MICROORGANISMS);

EID: 33645457953     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf052564y     Document Type: Article

References (31)

1. Burt, S. A. Essential oils: Their antibacterial properties and potential applications in foods - A review. Int. J. Food Microbiol. 2004, 94, 223-253.
2. Arrebola, M. L.; Navarro, M. C.; Jiménez, J.; Ocaña, F. A. Yield and composition of the essential oil of Thymus serpylloides subsp. serpylloides. Phytochemistry 1994, 36, 67-72.
3. Sökmen, M.; Serkedjieva, J.;Daferera, D.; Gulluce, M.; Polissiou, M.; Tepe, B.; Akpulat, H. A.; Sahin, F.; Sökmen A. In vitro antioxidant, antimicrobial, and antiviral activities of the essential oil and various extracts from herbal parts and callus cultures of Origanum acutidens. J. Agric. Food Chem. 2004, 52, 3309-3312.
4. Dorman, H. J.; Deans, S. G. Antimicrobial agents from plants: Antibacterial activity of plant volatile oils. J. Appl. Microbiol. 2000, 88, 308-316.
5. Friedman, M.; Henika, P. R.; Mandrell, R. E. Bactericidal activities of plant essential oils and some of their isolated constituents against Campylobacter jejuni, Escherichia coli, Listeria monocytogenes, and Salmonella enterica. J. Food Prot. 2002, 65, 1545-1560.
6. Chami, N.; Bennis, S.; Chami, F.; Aboussekhra, A.; Remmal, A. Study of anticandidal activity of carvacrol and eugenol in vitro and in vivo. Oral Microbiol. Immunol. 2005, 20, 106-111.
7. Tampieri, M. P.; Galuppi, R.; Macchioni, F.; Carelle, M. S.; Falcioni, L.; Cioni, P. L.; Morelli, I. The inhibition of Candida albicans by selected essential oils and their major components. Mycopathologia 2005, 59, 339-345.
8. Ultee, A.; Smid, E. J. Influence of carvacrol on growth and toxin production by Bacillus cereus. Int. J. Food Microbiol. 2001, 64, 373-378.
9. Ahn, Y. J.; Lee, S. B.; Lee, H. S.; Kim, G. H. Insecticidal and acaricidal activity of carvacrol and β-thujaplicine derived from Thujopsis dolabrata var. Hondai sawdust. J. Chem. Ecol. 1998, 24, 81-90.
10. Panella, N. A.; Dolan, M. C.; Karchesy, J. J.; Xiong, Y.; Peralta-Cruz, J.; Khasawneh, M.; Montenieri, J. A.; Maupin, G. O. Use of novel compounds for pest control: insecticidal and acaricidal activity of essential oil components from heartwood of Alaska yellow cedar. J. Med. Entomol. 2005, 42, 352-358.
11. Lindberg, C. M.; Melathopoulos, A. P.; Winston, M. L. Laboratory evaluation of miticides to control Varroa jacobsoni (Acari: Varroidae), a honey bee (Hymenoptera: Apidae) parasite. J. Econ. Entomol. 2000, 93, 189-198.
12. Allahverdiyev, A.; Duran, N.; Ozguven, M.; Koltas, S. Antiviral activity of the volatile oils of Melissa officinalis L. against Herpes simplex virus type-2. Phytomedicine 2004, 11, 657-661.
13. Garcia, C. C.; Talarico, L.; Almeida, N.; Colombres, S.; Duschatzky, C.; Damonte, E. B. Virucidal activity of essential oils from aromatic plants of San Luis, Argentina. Phytother. Res. 2003, 17, 1073-1075.
14. Helander, I. K.; Alakomi, H. L.; Latva-Kala, K.; Mattila-Sandholm, T.; Pol, I.; Smid, E. J.; von Wright, A. Characterization of the action of selected essential oil components on Gram-negative bacteria. J. Agric. Food Chem. 1998, 46, 3590-3595.
15. Ultee, A.; Bennik, M. H.; Moezelaar, R. The phenolic hydroxyl group of carvacrol is essential for action against the food-borne pathogen Bacillus cereus. Appl. Environ. Microbiol. 2002, 68, 1561-1568.
16. Wu, M.; Maier, E.; Benz, R.; Hancock, R. E. Mechanism of interaction of different classes of cationic antimicrobial peptides with planar bilayers and with the cytoplasmic membrane of Escherichia coli. Biochemistry 1999, 38, 7235-7242.
17. Burt, S. A.; Vlielander, R.; Haagsman, H. P.; Veldhuizen, E. J. A. Increase in activity of essential oil components carvacrol and thymol against Escherichia coli O157.H7 by addition of food stabilizers. J. Food Prot. 2005, 68, 919-926.
18. Cosentino, S.; Tuberoso, C. I.; Pisano, B.; Satta, M.; Mascia, V.; Arzedi, E.; Palmas, F. In-vitro antimicrobial activity and chemical composition of Sardinian Thymus essential oils. Lett. Appl. Microbiol. 1999, 29, 130-135.
19. Juliano, C.; Mattana, A.; Usai, M. Composition and in vitro antimicrobial activity of the essential oil of Thymus herba-barona Loisel growing wild in Sardinia. J. Essent. Oil Res. 2000, 12, 516-522.
20. Kim, J. M.; Marshall, M. R.; Wei, C. I. Antibacterial activity of some essential oil components against five foodborne pathogens. J. Agric. Food Chem. 1995, 43, 2839-2845.
21. Olasupo, N. A.; Fitzgerald, D. J.; Gasson, M. J.; Narbad, A. Activity of natural antimicrobial compounds against Escherichia coli and Salmonella enterica serovar Typhimurium. Lett. Appl. Microbiol. 2003, 37, 448-451.
22. Rivera-Carriles, K.; Argaiz, A.; Palou, E.; López-Malo, A. Synergistic inhibitory effect of citral with selected phenolics against Zygosaccharomyces bailii. J. Food Prot. 2005, 68, 602-606.
23. Ultee, A.; Kets, E. P.; Smid, E. J. Mechanisms of action of carvacrol on the food-borne pathogen Bacillus cereus. Appl. Environ. Microbiol. 1999, 65, 4606-4610.
24. Bagamboula, C. P.; Uyttendaele, M.; Debevere, J. Inhibitory effect of thyme and basil essential oils, carvacrol, thymol, estragol, linalool and p-cymene towards Shigella sonnei and S. flexneri. Food Microbiol. 2004, 21, 33-42.
25. Sivropoulou, A.; Papanikolaou, E.; Nikolaou, C.; Kokkini, S.; Lanaras, T.; Arsenakis, M. Antimicrobial and cytotoxic activities of oreganum essential oils. J. Agric. Food Chem. 1996, 44, 1202-1205.
26. Kiskó, G.; Roller, S. Carvacrol and p-cymene inactivate Escherichia coli O157:H7 in apple juice. BMC Microbiol. 2005, 5, 36.
27. Ultee, A.; Slump, R. A.; Steging, G.; Smid, E. J. Antimicrobial activity of carvacrol on rice. J. Food Prot. 2000, 63, 620-624.
28. Carson, C. F.; Riley, T. V. Antimicrobial activity of the major components of the essential oil of Melaleuca alternifolia. J. Appl. Bacteriol. 1995, 78, 264-269.
29. Sikkema, J.; de Bont, J. A. M.; Poolman, B. Mechanisms of membrane toxicity of hydrocarbons. Microbiol. Rev. 1995, 59, 201-222.
30. Farag, R. S.; Daw, Z. Y.; Hewedi, F. M.; El-Baroty, G. S. A. Antimicrobial activity of some Egyptian spice essential oils. J. Food Prot. 1989, 52, 665-667.
31. Juven, B. J.; Kanner, J.; Schved, F.; Weisslowicz, H. Factors that interact with the antibacterial action of thyme essential oil and its active constituents. J. Appl. Bacteriol. 1994, 76, 626-631.