Plant Protect. Sci., 2018, 54(1):9-16 | DOI: 10.17221/9/2017-PPS

Antifungal potential and biochemical effects of monoterpenes and phenylpropenes on plantOriginal Paper

Gehan I. Kh. Marei1, Samir. A. M. Abdelgaleil2*
1 Department of Pest Control and Environmental Protection, Faculty of Agriculture, Damanhour University, Damanhour, Egypt
2 Department of Pesticide Chemistry and Technology, Faculty of Agriculture, El-Shatby, Alexandria University, Alexandria, Egypt

To develop new natural fungicides, six monoterpenes and two phenylpropenes were tested for their antifungal activity against eight plant pathogenic fungi. The results of the mycelial growth inhibition assay showed that trans-cinnamaldehyde was the most potent compound against the eight tested fungi with EC50 values ranging between 0.75 and 3.19 mg/l. This compound caused the higher mycelial growth inhibition than carbendazim. Furthermore, (-)-menthone exhibited strong antifungal activity against Alternaria solani (EC50 = 9.31 mg/l), Penicillium digitatum (EC50 = 16.14 mg/l), and Rhizoctonia solani (EC50 = 24.69 mg/l). Likewise, eugenol showed potent antifungal activity against P. digitatum, R. solani, Fusarium solani, and A. solani, whereas EC50 values were less than 30.0 mg/l. In a separate experiment, trans-cinnamaldehyde, p-cymene, eugenol, and (-)-menthone were evaluated for their inhibitory effects on pectin methyl esterase and cellulase. The tested compounds exhibited the pronounced inhibition of enzyme activities with trans-cinnamaldehyde being the most potent inhibitor for both enzymes.

Keywords: natural products; antifungal activity; enzyme inhibition

Published: March 31, 2018  Show citation

ACS AIP APA ASA Harvard Chicago Chicago Notes IEEE ISO690 MLA NLM Turabian Vancouver
Marei GIK, Abdelgaleil SAM. Antifungal potential and biochemical effects of monoterpenes and phenylpropenes on plant. Plant Protect. Sci. 2018;54(1):9-16. doi: 10.17221/9/2017-PPS.
Share...
Download citation
  • BibTeX (.bib)
  • Bookends (.ris)
  • EasyBib (.ris)
  • EndNote (.enw)
  • EndNote 8 (.xml)
  • ISI WoS (.isi)
  • Medlars (.medlars)
  • Mendeley (.ris)
  • MODS (.xml)
  • Papers (.ris)
  • RefWorks (.txt)
  • RefManager (.ris)
  • RIS (.ris)
  • MS Word (.xml)
  • Zotero (.ris)
    • Open full article

    References

    1. Aoudou Y., Léopold T.N., Michel J.D.P., Xavier E.F., Moses M.C. (2010): Antifungal properties of essential oils and some constituents to reduce foodborne pathogen. Journal Yeast and Fungal Research, 1: 1-8.
    2. Bajpai V.K., Rahman A., Kang S.C. (2007): Chemical composition and anti-fungal properties of the essential oil and crude extracts of Metasequoia glyptostroboides Miki ex Hu. Industrial Crops and Products, 26: 28-35. Go to original source...
    3. Barrera-Necha L.L., Garduno-Pizana C., Garcia-Barrera L.J. (2009): In vitro antifungal activity of essential oils and their compounds on mycelial growth of Fusarium oxysporum f. sp. gladioli (Massey) Snyder and Hansen. Plant of Pathology Journal, 8: 17-21. Go to original source...
    4. Benzoukian P.Z. (1986): Perfumery and Flavoring Synthetics. Miami, Allured Publishing Co.
    5. Bouchra C., Achouri M., Idrissi Hassani L.M., Hmamouchi M. (2003): Chemical composition and antifungal activity of essential oils of seven Moroccan Labiatae against Botrytis cinerea Pers: Fr. Journal of Ethnopharmacology, 89: 165-169. Go to original source... Go to PubMed...
    6. Campaniello D., Corbo M.R., Sinigaglia M. (2010): Activity of eugenol against Penicillium, Aspergillus and Fusarium species. Journal of Food Protection, 73: 1124-1128. Go to original source... Go to PubMed...
    7. Cantore P.L., Shanmugaiah V., Iacobellis N.S. (2009): Antibacterial activity of essential oil components and their potential use in seed disinfection. Journal of Agriculture and Food Chemistry, 57: 9454-9461. Go to original source... Go to PubMed...
    8. Cheng S.-S., Liu J.-Y., Chang E.-H., Chang S.-T. (2008): Antifungal activity of cinnamaldehyde and eugenol congeners against wood-rot fungi. Bioresource Technology, 99: 5145-5149. Go to original source... Go to PubMed...
    9. Cox S.D., Mann C.M., Markham J.L., Bell H.C., Gustafson J.E., Warmington J.R., Wyllie S.G. (2000): The mode of antimicrobial action of the essential oil of Melaleuca alternifolia (tea tree oil). Journal of Applied Microbiology, 88: 170-175. Go to original source...
    10. De Martino L., Mancini E., Almeida L.F.R., De Feo V. (2010): The antigerminative activity of twenty-seven monoterpenes. Molecules, 15: 6630-6637. Go to original source... Go to PubMed...
    11. Duke S.O., Romagni J.G., Dayan F.E. (2000): Natural products as sources for new mechanisms of herbicidal action. Crop Protection, 19: 583-589. Go to original source...
    12. El-Zemity S.R., Ahmed S.M. (2005): Antifungal activity of some essential oils and their major chemical constituents against some phytopathogenic fungi. Journal of Pest Control and Environmental Science, 13: 87-99.
    13. Finney D.J. (1971): Probit Analysis. 3rd Ed. London, Cambridge University Press.
    14. Garcia R., Alves E.S.S., Santos M.P., Viegas Aquije G.M.F., Fernandes A.A.R., Dos Santos R.B., Ventura J.A., Fernandes P.M.B. (2008): Antimicrobial activity and potential use of monoterpenes as tropical fruits preservatives. Brazilian Journal of Microbiology, 39: 163-168. Go to original source...
    15. Grodnitzky J.A., Coats J.R. (2002): QSAR evaluation of monoterpenoids insecticidal activity. Journal of Agricultural and Food Chemistry, 50: 4576-4580. Go to original source... Go to PubMed...
    16. Harborne J.B., Baxter H. (1993): Phytochemical Dictionary, a Handbook of Bioactive Compounds from Plants. Taylor and Francis Ltd.
    17. Hartmans K.J., Diepenhorst P., Bakker W., Gorris L.G. M. (1995): The use of carvone in agriculture: sprout suppression of potatoes and antifungal activity against potato tuber and other plant diseases. Industrial Crops and Products, 4: 3-13. Go to original source...
    18. Kordali S., Kotan R., Cakir A. (2007): Screening of antifungal activities of 21 oxygenated monoterpenes in-vitro as plant disease control agents. Allelopathy Journal, 19: 373-392.
    19. Kordali S., Cakir A., Ozer H., Cakmakci R., Kesdek M., Mete E. (2008): Antifungal, phytotoxic and insecticidal properties of essential oil isolated from Turkish Origanum acutidens and its three components, carvacrol, thymol and p-cymene. Bioresource Technology, 99: 8788-8795. Go to original source... Go to PubMed...
    20. Marei G.I.KH., Abdel Rasoul M.A., Abdelgaleil S.A.M. (2012): Comparative antifungal activities and biochemical effects of monoterpenes on plant pathogenic fungi. Pesticide Biochemistry and Physiology, 103: 56-61. Go to original source...
    21. Morcia C., Malanati M., Terzi V. (2012): In vitro activity of terpinen-4-ol, eugenol, carvone, 1,8-cineole (eucalyptol) and thymol against mycotoxigenic plant pathogens. Food Additives and Contaminants, 29: 415-422. Go to original source... Go to PubMed...
    22. Pandey D.K., Tripathi N.N., Tripathi R.D., Dixit S.N.Z. (1982): Fungitoxic and phytotoxic properties of essential oil of Hyptis suaveolens. Zeitschrift für Pflanzenkrankheiten und Pflanzenschutz/Journal of Plant Diseases and Protection, 89: 344-349.
    23. Prashar A., Hili P., Veness R.G., Evans C.S. (2003): Antimicrobial action of palmarosa oil (Cymbopogon martinii) on Saccharomyces cerevisiae. Phytochemistry, 63: 569-575. Go to original source... Go to PubMed...
    24. Sikkema J., De Bont J.A., Poolman B. (1994): Interactions of cyclic hydrocarbons with biological membranes. Journal Biological Chemistry, 269: 8022-8028. Go to original source...
    25. Talboys P.W., Busch L.U. (1970): Pectic enzymes produced by Verticillium species. Transactions of the British Mycological Society, 55: 367-381. Go to original source...
    26. Templeton W. (1969): An Introduction of Chemistry of Terpenoids and Steroids. London, Butterworth.
    27. Tsao H., Coats J.R. (1995): Starting from nature to make better insecticides. ChemTech, 25: 23-28.
    28. Tsao R., Zhou T. (2000): Antifungal activity of monoterpenoids against postharvest pathogens Botrytis cinerea and Monilinia fructicola. Journal of Essential Oil Research, 12: 113-121. Go to original source...
    29. Uribe S., Ramirez J., Pena A. (1985): Effects of beta-pinene on yeast membrane functions. Journal of Bacteriology, 161: 1195-1200. Go to original source... Go to PubMed...
    30. Vokou D., Douvli P., Blionis G.J., Halley J.M. (2003): Effects of monoterpenoids, acting alone or in pairs, on seed germination and subsequent seedling growth. Journal of Chemical Ecology, 29: 2281-2301. Go to original source... Go to PubMed...
    31. Wang S.Y., Chen P.F., Chang S.T. (2005): Antifungal activities of essential oils and their constituents from indigenous cinnamon (Cinnamomum osmophloeum) leaves against wood decay fungi. Bioresource Technology, 96: 813-818. Go to original source...
    32. Wuryatmo E., Klieber A., Scott E. (2003): Inhibition of citrus post-harvest pathogens by vapor of citral and related compounds in culture. Journal of Agricultural and Food Chemistry, 51: 2637-2640. Go to original source... Go to PubMed...
    33. Zambonelli A., Zechini D., Aulerio A., Bianchi A., Albasini A. (1996): Effects of essential oils on phytopathogenic fungi in vitro. Phytopathology, 144: 491-494. Go to original source...
    34. Zhao L., Yany X., LI X., Mu W., Liu F. (2011): Antifungal, insecticidal and herbicidal properties of volatile components from Paenibacillus polymyxa strain BMP-11. Agricultural Sciences in China, 10: 728-736. Go to original source...

    This is an open access article distributed under the terms of the Creative Commons Attribution-NonCommercial 4.0 International (CC BY NC 4.0), which permits non-comercial use, distribution, and reproduction in any medium, provided the original publication is properly cited. No use, distribution or reproduction is permitted which does not comply with these terms.


    Return to the content