Antifungal potential and biochemical effects of monoterpenes and phenylpropenes on plant

https://doi.org/10.17221/9/2017-PPSCitation:Marei G.I.Kh., Abdelgalei S.A.M.: (2018): Antifungal potential and biochemical effects of monoterpenes and phenylpropenes on plant. Plant Protect. Sci., 54: 9-16.
download PDF
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.
References:
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.
 
Bajpai Vivek K., Rahman Atiqur, Kang Sun Chul (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 https://doi.org/10.1016/j.indcrop.2006.12.012
 
Barrera-Ne L.L., Garduno-Pi C., Garcia-Bar 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 Pathology Journal, 8, 17-21 https://doi.org/10.3923/ppj.2009.17.21
 
Benzoukian P.Z. (1986): Perfumery and Flavoring Synthetics. Miami, Allured Publishing Co.
 
Bouchra Chebli, Achouri Mohamed, Idrissi Hassani L.M, Hmamouchi Mohamed (2003): Chemical composition and antifungal activity of essential oils of seven Moroccan Labiatae against Botrytis cinerea Pers: Fr.. Journal of Ethnopharmacology, 89, 165-169 https://doi.org/10.1016/S0378-8741(03)00275-7
 
CAMPANIELLO DANIELA, CORBO MARIA ROSARIA, SINIGAGLIA MILENA (2010): Antifungal Activity of Eugenol against Penicillium, Aspergillus, and Fusarium Species. Journal of Food Protection, 73, 1124-1128 https://doi.org/10.4315/0362-028X-73.6.1124
 
Lo Cantore Pietro, Shanmugaiah Vellasamy, Iacobellis Nicola Sante (2009): Antibacterial Activity of Essential Oil Components and Their Potential Use in Seed Disinfection. Journal of Agricultural and Food Chemistry, 57, 9454-9461 https://doi.org/10.1021/jf902333g
 
Cheng Sen-Sung, Liu Ju-Yun, Chang Ed-Haun, Chang Shang-Tzen (2008): Antifungal activity of cinnamaldehyde and eugenol congeners against wood-rot fungi. Bioresource Technology, 99, 5145-5149 https://doi.org/10.1016/j.biortech.2007.09.013
 
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 https://doi.org/10.1046/j.1365-2672.2000.00943.x
 
Martino Laura De, Mancini Emilia, Almeida Luiz Fernando Rolim de, Feo Vincenzo De (2010): The Antigerminative Activity of Twenty-Seven Monoterpenes. Molecules, 15, 6630-6637 https://doi.org/10.3390/molecules15096630
 
Duke Stephen O, Romagni Joanne G, Dayan Franck E (2000): Natural products as sources for new mechanisms of herbicidal action. Crop Protection, 19, 583-589 https://doi.org/10.1016/S0261-2194(00)00076-4
 
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.
 
Finney D.J. (1971): Probit Analysis. 3rd Ed. London, Cambridge University Press.
 
Garcia Roxana, Alves Eliomara S.S., Santos Mirella P., Aquije Glória M.F. Viégas, Fernandes A. Alberto R., Santos Reginaldo B. dos, Ventura Jose A., Fernandes Patricia M.B. (2008): Antimicrobial activity and potential use of monoterpenes as tropical fruits preservatives. Brazilian Journal of Microbiology, 39, 163-168 https://doi.org/10.1590/S1517-83822008000100032
 
Grodnitzky Justin A., Coats Joel R. (2002): QSAR Evaluation of Monoterpenoids' Insecticidal Activity. Journal of Agricultural and Food Chemistry, 50, 4576-4580 https://doi.org/10.1021/jf0201475
 
Harborne J.B., Baxter H. (1993): Phytochemical Dictionary, a Handbook of Bioactive Compounds from Plants. Taylor and Francis Ltd.
 
Hartmans Klaasje J., Diepenhorst Peter, Bakker Willem, Gorris Leon 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 https://doi.org/10.1016/0926-6690(95)00005-W
 
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.
 
Kordali Saban, Cakir Ahmet, Ozer Hakan, Cakmakci Ramazan, Kesdek Memis, Mete Ebru (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 https://doi.org/10.1016/j.biortech.2008.04.048
 
Marei Gehan I.Kh., Abdel Rasoul Mona A., Abdelgaleil Samir A.M. (2012): Comparative antifungal activities and biochemical effects of monoterpenes on plant pathogenic fungi. Pesticide Biochemistry and Physiology, 103, 56-61 https://doi.org/10.1016/j.pestbp.2012.03.004
 
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.
 
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.
 
Prashar Anjali, Hili Pauline, Veness Robert G, Evans Christine S (2003): Antimicrobial action of palmarosa oil (Cymbopogon martinii) on Saccharomyces cerevisiae. Phytochemistry, 63, 569-575 https://doi.org/10.1016/S0031-9422(03)00226-7
 
Sikkema J., De Bont J.A., Poolman B. (1994): Interactions of cyclic hydrocarbons with biological membranes. Journal Biological Chemistry, 269: 8022–8028.
 
Talboys P.W., Busch L.V. (1970): Pectic enzymes produced by Verticillium species. Transactions of the British Mycological Society, 55, 367-381 https://doi.org/10.1016/S0007-1536(70)80058-4
 
Templeton W. (1969): An Introduction of Chemistry of Terpenoids and Steroids. London, Butterworth.
 
Tsao H., Coats J.R. (1995): Starting from nature to make better insecticides. ChemTech, 25: 23–28.
 
Tsao Rong, Zhou Ting (2000): Antifungal Activity of Monoterpenoids against Postharvest Pathogens Botrytis cinerea and Monilinia fructicola. Journal of Essential Oil Research, 12, 113-121 https://doi.org/10.1080/10412905.2000.9712057
 
Uribe S., Ramirez J., Pena A. (1985): Effects of beta-pinene on yeast membrane functions. Journal of Bacteriology, 161: 1195–1200.
 
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.https://doi.org/10.1023/A:1026274430898
 
Wang Sheng-Yang, Chen Pin-Fun, Chang Shang-Tzen (2005): Antifungal activities of essential oils and their constituents from indigenous cinnamon (Cinnamomum osmophloeum) leaves against wood decay fungi. Bioresource Technology, 96, 813-818 https://doi.org/10.1016/j.biortech.2004.07.010
 
Wuryatmo Erminawati, Klieber Andreas, Scott Eileen S. (2003): Inhibition of Citrus Postharvest Pathogens by Vapor of Citral and Related Compounds in Culture. Journal of Agricultural and Food Chemistry, 51, 2637-2640 https://doi.org/10.1021/jf026183l
 
Zambonelli A., D'Aulerio A. Zechini, Bianchi A., Albasini A. (1996): Effects of Essential Oils on Phytopathogenic Fungi In Vitro. Journal of Phytopathology, 144, 491-494 https://doi.org/10.1111/j.1439-0434.1996.tb00330.x
 
ZHAO Li-jing, YANG Xiao-nan, LI Xiang-ying, MU Wei, LIU Feng (2011): Antifungal, Insecticidal and Herbicidal Properties of Volatile Components from Paenibacillus polymyxa Strain BMP-11. Agricultural Sciences in China, 10, 728-736 https://doi.org/10.1016/S1671-2927(11)60056-4
 
download PDF

© 2018 Czech Academy of Agricultural Sciences