1887

Abstract

Eugenol, the main component of clove bud essential oil () has been linked to antimicrobial, anti-inflammatory, insecticidal and immunomodulatory properties. The purpose of this study was to evaluate the antifungal and cytotoxic activity of eugenol, the essential oil of , and some semisynthetic derivatives of eugenol against dermatophytes of the genus .

We evaluated the antifungal effect of the compounds, determining the minimum inhibitory concentrations (MICs) by the microdilution method and the minimum fungicidal concentrations by cultures from the inhibitions. Additionally, the inhibition of the radial growth of the mycelium of the dermatophyte fungi was tested by poisoned substrate. Cytotoxicity was measured by the colorimetric method on Vero cells.

All of the eugenol compounds tested exhibited antifungal properties, showing MICs of 62.5–500 µg ml , determined within three dermatophyte species: and . Among these derivatives, methyl isoeugenol, at concentrations of 300 and 100 µg ml, was found to completely inhibit (100 %) radial growth of the mycelium of all three species after 20 days of treatment. Additionally, phenotypic variations related to the decrease in pigment production of were observed after treatment with O-ethyl and O-butyl isoeugenol derivatives. Meanwhile, all of the tested (iso)eugenol molecules exhibited moderate toxicity in Vero cells [50 % cytotoxic concentration (the concentration required for a 50 % reduction in cell viability; CC): 54.06–265.18 µg ml ).

The results suggest that the semisynthetic eugenol derivatives (SEDs) show promising antifungal activity and selectivity against dermatophyte fungi.

Loading

Article metrics loading...

/content/journal/jmm/10.1099/jmm.0.001019
2019-07-01
2024-03-29
Loading full text...

Full text loading...

/deliver/fulltext/jmm/68/7/1109.html?itemId=/content/journal/jmm/10.1099/jmm.0.001019&mimeType=html&fmt=ahah

References

  1. Nenoff P, Krüger C, Schaller J, Ginter-Hanselmayer G, Schulte-Beerbühl R et al. Mycology - an update part 2: dermatomycoses: clinical picture and diagnostics. J Dtsch Dermatol Ges 2014; 12:749–777 [View Article]
    [Google Scholar]
  2. de Hoog GS, Dukik K, Monod M, Packeu A, Stubbe D et al. Toward a novel multilocus phylogenetic taxonomy for the dermatophytes. Mycopathologia 2017; 182:5–31 [View Article]
    [Google Scholar]
  3. Deepika TL, Kannabiran K. Review on dermatomycosis: pathogenesis and treatment. Natural Science 2010; 2:726–731
    [Google Scholar]
  4. Molina de Diego A. Aspectos clínicos, diagnósticos Y terapéuticos de las dermatofitosis. Enferm Infecc Microbiol Clin 2011; 29:33–39 [View Article]
    [Google Scholar]
  5. Marchese A, Barbieri R, Coppo E, Orhan IE, Daglia M et al. Antimicrobial activity of eugenol and essential oils containing eugenol: a mechanistic viewpoint. Crit Rev Microbiol 2017; 43:668–689 [View Article]
    [Google Scholar]
  6. National Committee for Clinical Laboratory Standards Reference method for broth dilution antifungal susceptibility testing of yeasts, Approved standard NCCLS document M27-A. Wayne, PA: National Committee for Clinical Laboratory Standards; 1997
    [Google Scholar]
  7. Leal SM, Herrera LV, Vargas LY. In vitro susceptibility of Microsporum spp. and mammalian cells to Eugenia caryophyllus essential oil, eugenol and semisynthetic derivatives. Mycoses 20181–10
    [Google Scholar]
  8. Pavela R. Acute, synergistic and antagonistic effects of some aromatic compounds on the Spodoptera littoralis Boisd. (Lep., Noctuidae) larvae. Ind Crops Prod 2014; 60:247–258 [View Article]
    [Google Scholar]
  9. Chaieb K, Hajlaoui H, Zmantar T, Kahla-Nakbi AB, Rouabhia M et al. The chemical composition and biological activity of clove essential oil, Eugenia caryophyllata (Syzigium aromaticum L. Myrtaceae): a short review. Phytother Res 2007; 21:501–506 [View Article]
    [Google Scholar]
  10. Gülçin İlhami, Gülçin I. Antioxidant activity of eugenol: a structure-activity relationship study. J Med Food 2011; 14:975–985 [View Article]
    [Google Scholar]
  11. Han X, Parker TL. Anti-inflammatory activity of clove (Eugenia caryophyllata) essential oil in human dermal fibroblasts. Pharm Biol 2017; 55:1619–1622 [View Article]
    [Google Scholar]
  12. Mahakittikun V, Soonthornchareonnon N, Foongladda S, Boitano JJ, Wangapai T et al. A preliminary study of the acaricidal activity of clove oil, Eugenia caryophyllus . Asian Pac J Allergy Immunol 2014; 32:46–52
    [Google Scholar]
  13. Seixas FJ, da Franca Rodrigues KA, Guerra de Oliveira R et al. Synthesis and in vitro Anti Leishmania amazonensis biological screening of Morita-Baylis-Hillman adducts prepared from eugenol, thymol and carvacrol. Molecules 2016; 21:1483
    [Google Scholar]
  14. Vermout S, Tabart J, Baldo A, Mathy A, Losson B et al. Pathogenesis of dermatophytosis. Mycopathologia 2008; 166:267–275 [View Article]
    [Google Scholar]
  15. Martínez-Rossi NM, Peres NTA, Rossi A. Pathogenesis of dermatophytosis: sensing the host tissue. Mycopathologia 2017; 182:215–227 [View Article]
    [Google Scholar]
  16. Brand A. Hyphal growth in human fungal pathogens and its role in virulence. Int J Microbiol 2012; 166:267–275
    [Google Scholar]
  17. Yamada T, Maeda M, Alshahni MM, Tanaka R, Yaguchi T et al. Terbinafine resistance of Trichophyton clinical isolates caused by specific point mutations in the squalene epoxidase gene. Antimicrob Agents Chemother 2017; 61:e00115–00117 [View Article]
    [Google Scholar]
  18. Christenson J, Peterson G, Naunton M, Bushell M, Kosari S et al. Challenges and opportunities in the management of onychomycosis. J Fungi 2018; 4:87 [View Article]
    [Google Scholar]
  19. Gupta AK, Cernea M, Foley KA. Improving cure rates in onychomycosis. J Cutan Med Surg 2016; 20:517–531 [View Article]
    [Google Scholar]
  20. Summerbell RC. Form and function in the evolution of dermatophytes. In Kushwaha RKS, Guarro J. (editors) Biology of dermatophytes and other keratinolytic fungi, Iberoamericana de Micología.
    [Google Scholar]
  21. Guoling Y, Xiaohong Y, Jingrong L, Liji J, Lijia A. A study on stability of phenotype and genotype of Trichophyton rubrum . Mycopathologia 2006; 161:205–212 [View Article]
    [Google Scholar]
  22. de Oliveira Pereira F, Mendes JM, de Oliveira Lima E. Investigation on mechanism of antifungal activity of eugenol against Trichophyton rubrum . Med Mycol 2013; 51:507–513 [View Article]
    [Google Scholar]
  23. Gayoso CW, Lima EO, Oliveira VT, Pereira FO, Souza EL et al. Sensitivity of fungi isolated from onychomycosis to Eugenia cariophyllata essential oil and eugenol. Fitoterapia 2005; 76:247–249 [View Article]
    [Google Scholar]
  24. Pinto E, Vale-Silva L, Cavaleiro C, Salgueiro L. Antifungal activity of the clove essential oil from Syzygium aromaticum on Candida, Aspergillus and dermatophyte species. J Med Microbiol 2009; 58:1454–1462 [View Article]
    [Google Scholar]
  25. Rana IS, Rana AS, Rajak RC. Evaluation of antifungal activity in essential oil of the Syzygium aromaticum (L.) by extraction, purification and analysis of its main component eugenol. Braz J Microbiol 2011; 42:1269–1277 [View Article]
    [Google Scholar]
  26. Fernández-Torres B, Cabañes FJ, Carrillo-Muñoz AJ, Esteban A, Inza I et al. Collaborative evaluation of optimal antifungal susceptibility testing conditions for dermatophytes. J Clin Microbiol 2002; 40:3999–4003 [View Article]
    [Google Scholar]
  27. Binh LT, Beaufay C, Trong ND et al. In vitro anti-leishmanial activity of essential oils extracted from Vietnamese plants. Molecules 2017; 22:1071
    [Google Scholar]
  28. Prashar A, Locke IC, Evans CS. Cytotoxicity of clove (Syzygium aromaticum) oil and its major components to human skin cells. Cell Prolif 2006; 39:241–248 [View Article]
    [Google Scholar]
  29. Yoo CB, Han KT, Cho KS, Ha J, Park HJ et al. Eugenol isolated from the essential oil of Eugenia caryophyllata induces a reactive oxygen species-mediated apoptosis in HL-60 human promyelocytic leukemia cells. Cancer Lett 2005; 225:41–52 [View Article]
    [Google Scholar]
http://instance.metastore.ingenta.com/content/journal/jmm/10.1099/jmm.0.001019
Loading
/content/journal/jmm/10.1099/jmm.0.001019
Loading

Data & Media loading...

Supplements

Supplementary material 1

PDF
This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error