Isolation and identification of phenolic compounds from Eugenia caryophyllus and study on its biological effect against Macrophomina phaseolina
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Abstract
Clove is one of the oldest and most famous spices. Its seeds resemble nails. It is used in medicinal fields, but its fungicidal activity is unknown. The aim of the study was to test the inhibitory activity of phenolic extracts of cloves against the pathogenic fungus Macrophomina phaseolina. The research was conducted under laboratory conditions to test the inhibitory ability of Eugenia caryophyllus phenolic extracts on the fungus M. phaseolina, which was partially diagnosed on strawberry plants based on Polymerase chain reaction (PCR) technique, in addition to its morphological and microscopic characteristics. The active compounds present The active compounds (Chlorogenic acid, Qurcetine, Gallic acid, Apigenin, Caffeic acid, Ferulic acid, Kaempferol, Rutin, Catechine) present in the extract of Industrial Methylated Spirit (IMS) separated from cloves were determined using High-performance liquid chromatography (HPLC). and active compounds of IMS phenols) Qurcetine, Apigenin, Ferulic acid, Kaempferol. (The inhibitory effect of phenols extracted from E. caryophyllus against M. phaseolina was tested. The results showed that the acetone extract and acetone phenols, which were used at concentrations of 10 and 15 mg/ml in PDA medium, had a significant effect on the growth of the fungus by 100%, as these fungi failed to grow. Formation of spores on Peptone dextrose medium (PDA) medium. While the percentage of inhibition of acetone phenols was 25% at a concentration of 5 mg/ml. As for the IMS extract and IMS phenols, it had a significant effect on the growth of the fungus at all concentrations used, but with different inhibition ratios, which increased directly with increasing concentration of the extract.
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Keywords
Eugenia caryophyllus , Extract, High-performance liquid chromatography (HPLC) , Microphobia phaseolina, Polymerase chain reaction ( PCR)
References
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Agrios, G.N. (2005). ''Plant Pathology''. 5th ed. Elsevier Academic Press, Burlington, U.S.A., 922 p.
Al-Ameri, H. A., Dawood, Z. A. & Abed, F. N. M. (2018). Isolation and Identification of Fungi From Strawberry Seedlings and its Biological Agent and Fungicides. Rafidain Journal of Science, 27(1), 82-94. DOI : 10.33899/RJS.2018.141075
Al-Daody, A.Ch. (1998). Chemical Study on some Iraqi Plants. Ph.D. Thesis, College of Science, University of Mosul, 112-113.
Al-dulaimi, F. K. & AL-Tarjuman, J. K. (2020). Effects of cordyceps sinensis fungus on some physiological parameters of mice infected by acrylamide. Biochemical & Cellular Archives, 20(1), 1463-1466, DOI : 10.35124/bca.2020.20.1.1463
Al-dulaimi, F.K.Y., AL-Tarjuman , J.K. & MullaAbid , F.N. (2020). Inhibitory activity of Saccharomyces cerevisiae, Rhodotorulaglutinis and Lactobacillus spp against Escherichia coli isolated from children diarrhea infection. Biochem. Cell. Arch .23(7), 1-4. DOI: 10.36295/ASRO.2020.23714.
Al–Handel, S. S. H. & Ghanim, N. S. (2021). Effect of Organic Fertilizer levels and Spraying by Gibberellic on growth and yield characterstics of Strawberry Plant Fragaria X Ananassa Duch. in Gypsum Soil. Kirkuk University Journal For Agricultural Sciences, 12(1), 47-55. D0I: 10.58928/KU21.12106
Al-Juboory, H. H., Hassan, A. K. & El-Humeiri, Y. N. (2018). Effect of some bioinducers in controlling the pathogen M. phaseolina that causes root and stem charcoal rot of strawberry. Arab Journal of Plant Protection, 36(2), 154-163.DOI: 10.22268/AJPP-036.2.154163
AL-Tarjuman, J. K. ; Ramadan, N. A. & Nader, M. I.(2017). Antagonism Efficiency of Trichoderma against Rhizactoni solani-15 and Molecular Diagnosed. European AcademicRresearch ISSN 2286-4822.
Al-Tarjuman,J.K.; Mula Abed,F.N. & AL-Dulaimi,F.K.Y . (2020). Study on fungal contamination of Iraqi paper currency. Biochem. Cell. Arch.20( 1): 2201-2208.
Andrade, R.G.; Ginani, J. S.; Lopes, G.K.B.; Butra, F.; Alonso, A. & Hermes Lima, M. (2006). Tannic acid inhibits In vitro iron – dependent free radical formation. Biochemic., 88: 1287-1296. DOI: 10.1016/j.biochi.2006.02.006
Bhowmik , D., Kumar,K.P.,Yaday,A., Srivastava,S. & Paswan,S.(2012).Recent trends in Indian traditional herbs Syzgium aromaticum and its health benefits . J.Pharmacognosy and Phytochemistry, 1(2), 6-17.
Cortés-Rojas, D. F., de Souza, C. R. F. & Oliveira, W. P. (2014). Clove (Syzygium aromaticum): a precious spice. Asian Pacific Journal ofTtropicalBbiomedicine, 4(2), 90-96. DIO: 10.1016/S2221-1691(14)60215-X
Dawar, S., Hayat, S., Anis, M. & Zaki, M. J. (2008). Effect of seed coating material in the efficacy of microbial antagonists for the control of root rot fungi on okra and sunflower. Pak. J. Bot, 40(3), 1269-1278.
Ehteshamul‐Haque, S. & Ghaffar, A. (1993). Use of rhizobia in the control of root rot diseases of sunflower, okra, soybean and mungbean. Journal of Phytopathology, 138(2), 157-163. https://doi.org/10.1111/j.1439-0434.1993.tb 01372.x
Ellis, M.B. 1971. Dematiaceous Hyphomycetes. Commonwealth Mycological Institute Kew , survey England .608 pp. exudates on fluorescent Pseudomodad sand fungi in solarized soil. Phytopathology, 82, 320 – 327.
El-Saber Batiha, G., Alkazmi, L. M., Wasef, L. G., Beshbishy, A. M., Nadwa, E. H, & Rashwan, E. K. (2020). Syzygium aromaticum L.(Myrtaceae): traditional uses, bioactive chemical constituents, pharmacological and toxicological activities. Biomolecules, 10(2), 202. DOI: 10.3390/biom10020202
Hashim, S. T., Hamza, I. S. & Hassan, M. A. (2013). Appreciation quantitative chemical compounds phenolic extract of the seeds of Syzgium aromaticum and study its inhibitory effect in some food-born pathogenic bacteria. The Iraqi Journal of Veterinary Medicine, 37(2).
Herborne, J. B. (1973). Phytochemical methods. A Guide to Modern Techniques of Plant Analysis, 2, 5-11.
Jimoh, S. O., Arowolo, L. A. & Alabi, K. A. (2017). Phytochemical screening and antimicrobial evaluation of Syzygium aromaticum extract and essential oil. Int. J. Curr. Microbiol. Appl. Sc.i, 6, 4557-4567. https://doi.org/10.20546/ijcmas.2017.607.432
Khoddami, A., Wilkes, M. A. & Roberts, T. H. (2013). Techniques for analysis of plant phenolic compounds. Molecules, 18(2), 2328-2375. doi: 10.3390/molecules18022328.
Kumar, K.P.; Yadav, A.; Srivastava, S.; Paswan, S. & Dutt, A.S. (2012). Recent trends in Indian traditional herbs Syzygium aromaticum and health benefits. J. Pharmacongnocy and Phytochemistry, 1(1), 6-17.
Lavanya, N., & Kelaiya, D. S. (2022). Evaluation of different bio control agents against root rot incidence of castor incited by Macrophomina phaseolina (Tassi) Goid. The Pharma Innovation Journal, 11(8), 955-959.https://www.thepharmajournal.com/archives/2022/vol11issue8/PartL/11-8-22-728.pdf
Le, D. T. & Vu, N. T. (2017). Progress of loop-mediated isothermal amplification technique in molecular diagnosis of plant diseases. Applied Biological Chemistry, 60(2), 169-180. http://dx.doi.org/10.1007%2Fs13765-017-0267-y
Leslie,J.F. & Summerell, B.A. (2006) .The Fusarium Laboratory Manual . Black well Publishing . 388 pp. DOI:10.1002/9780470278376
Mashkor, I. M. A. A. (2015). Evaluation of antioxidant activity of clove (Syzygium aromaticum). Int. J. Chem. Sci, 13(1), 22-30.
Mitscher, L. A., Leu, R. P., Bathala, M. S., Wu, W. N. & Beal, J. L. (1972). Antimicrobial agents from higher plants. I. Introduction, rationale, and methodology. Lloydia, 35(2), 157-166.
Moradi, E., Rakhshandeh, H., Rahimi Baradaran, V., Ghadiri, M., Hasanpour, M., Iranshahi, M. & Askari, V. R. (2023). HPLC/MS characterization of Syzygium aromaticum L. and evaluation of its effects on peritoneal adhesion: Investigating the role of inflammatory cytokines, oxidative factors, and fibrosis and angiogenesis biomarkers. Physiological Reports, 11(2), e15584. doi: 10.14814/phy2.15584.
Najm, M. R, & Sultan, F. I. (2022). Evaluation of Phytochemical Constituents by GC-MS, HPLC and Biological Activity of Peganum Harmala L. Seeds Extract. In IOP Conference Series: Earth and Environmental Science (Vol. 1060, No. 1, p. 012097). IOP Publishing. DOI 10.1088/1755-1315/1060/1/012097
Pitt, J. I. & Hocking, A. D. (2009). Fungi and food spoilage (Vol. 519, p. 388). New York: Springer. https://doi.org/10.1007/978-0-387-92207-2
Razem, M., Ding, Y., Morozova, K., Mazzetto, F. & Scampicchio, M. (2022). Analysis of Phenolic Compounds in Food by Coulometric Array Detector: A Review. Sensors, 22(19), 7498. DOI: 10.3390/s22197498
Sánchez, S., Chamorro, M., Henríquez, J. L., Grez, J., Díaz, I., Santos, B. D. L. & Gambardella, M. (2017). Genetic and biological characterization of Macrophomina phaseolina (Tassi) Goid. causing crown and root rot of strawberry. Chilean journal of Agricultural Research, 77(4), 325-331. http://dx.doi.org/10.4067/S0718-58392017 000400325
Shoko, T.; Soich, T., Megumi, M.M.; Eri, E.; Jun, K. & Michika, W. (1999) Isolation and identification of an antibacterial compound from grape and its application to foods. Noppon Nogeikagaku Kaishi, 73, 125-128. DOI:10.1271/NOGEIKAGAKU1924.73.125Jafeer, K. A. M. M. & Kheirallah, E. A. (2016). Effect of Piper Nigrum fruit and Syzygium aromaticum roses extract on the some of Bacterial and fungal isolate growth. Al-Qadisiyah Journal of Pure Science, 21(2), 36-45
Soto-Vaca, A., Gutierrez, A., Losso, J. N., Xu, Z. & Finley, J. W. (2012). Evolution of phenolic compounds from color and flavor problems to health benefits. Journal of agricultural and food chemistry, 60(27), 6658-6677. https://doi.org/10.1021/jf300861c
Sultan, F.I. (2020). Phytochemical analysis and antibacterial activities of Frankincense of Boswellia serrate. Plant Archives, 20(2): 5219-5226.
Sultan, F.I.; Al-Farha, A.A. & Shaaban, I. (2020A). Separation and identification of some fatty acids and phenolic compounds from Portulaca oleracea L. and study their biological effect on two types of pathogenic bacteria. Asian J. Agric & Biol. AJAB. 8(3): 1-1. DOI: 10.35495/ajab.2020.02.119
Takó M, Kerekes EB, Zambrano C, Kotogán A, Papp T, Krisch J, Vágvölgyi C. (2020). Plant phenolics & phenolic-enriched extracts as antimicrobial agents against food-contaminating microorganisms. Antioxidants (Basel). 9(2),165. doi: 10.3390/antiox9020165. PMID: 32085580; PMCID: PMC7070704.
Yousif, A. A. & Hassan, W. A. (2023). HPLC ANALYSIS AND ANTIFUNGAL ACTIVITY OF SOME PLANT EXTRACTS AGAINST DECAY APPLE FRUITS. Iraqi Journal of Agricultural Sciences, 54(1), 291-302. https://doi.org/10.36103/ijas.v54i1.1702
Agrios, G.N. (2005). ''Plant Pathology''. 5th ed. Elsevier Academic Press, Burlington, U.S.A., 922 p.
Al-Ameri, H. A., Dawood, Z. A. & Abed, F. N. M. (2018). Isolation and Identification of Fungi From Strawberry Seedlings and its Biological Agent and Fungicides. Rafidain Journal of Science, 27(1), 82-94. DOI : 10.33899/RJS.2018.141075
Al-Daody, A.Ch. (1998). Chemical Study on some Iraqi Plants. Ph.D. Thesis, College of Science, University of Mosul, 112-113.
Al-dulaimi, F. K. & AL-Tarjuman, J. K. (2020). Effects of cordyceps sinensis fungus on some physiological parameters of mice infected by acrylamide. Biochemical & Cellular Archives, 20(1), 1463-1466, DOI : 10.35124/bca.2020.20.1.1463
Al-dulaimi, F.K.Y., AL-Tarjuman , J.K. & MullaAbid , F.N. (2020). Inhibitory activity of Saccharomyces cerevisiae, Rhodotorulaglutinis and Lactobacillus spp against Escherichia coli isolated from children diarrhea infection. Biochem. Cell. Arch .23(7), 1-4. DOI: 10.36295/ASRO.2020.23714.
Al–Handel, S. S. H. & Ghanim, N. S. (2021). Effect of Organic Fertilizer levels and Spraying by Gibberellic on growth and yield characterstics of Strawberry Plant Fragaria X Ananassa Duch. in Gypsum Soil. Kirkuk University Journal For Agricultural Sciences, 12(1), 47-55. D0I: 10.58928/KU21.12106
Al-Juboory, H. H., Hassan, A. K. & El-Humeiri, Y. N. (2018). Effect of some bioinducers in controlling the pathogen M. phaseolina that causes root and stem charcoal rot of strawberry. Arab Journal of Plant Protection, 36(2), 154-163.DOI: 10.22268/AJPP-036.2.154163
AL-Tarjuman, J. K. ; Ramadan, N. A. & Nader, M. I.(2017). Antagonism Efficiency of Trichoderma against Rhizactoni solani-15 and Molecular Diagnosed. European AcademicRresearch ISSN 2286-4822.
Al-Tarjuman,J.K.; Mula Abed,F.N. & AL-Dulaimi,F.K.Y . (2020). Study on fungal contamination of Iraqi paper currency. Biochem. Cell. Arch.20( 1): 2201-2208.
Andrade, R.G.; Ginani, J. S.; Lopes, G.K.B.; Butra, F.; Alonso, A. & Hermes Lima, M. (2006). Tannic acid inhibits In vitro iron – dependent free radical formation. Biochemic., 88: 1287-1296. DOI: 10.1016/j.biochi.2006.02.006
Bhowmik , D., Kumar,K.P.,Yaday,A., Srivastava,S. & Paswan,S.(2012).Recent trends in Indian traditional herbs Syzgium aromaticum and its health benefits . J.Pharmacognosy and Phytochemistry, 1(2), 6-17.
Cortés-Rojas, D. F., de Souza, C. R. F. & Oliveira, W. P. (2014). Clove (Syzygium aromaticum): a precious spice. Asian Pacific Journal ofTtropicalBbiomedicine, 4(2), 90-96. DIO: 10.1016/S2221-1691(14)60215-X
Dawar, S., Hayat, S., Anis, M. & Zaki, M. J. (2008). Effect of seed coating material in the efficacy of microbial antagonists for the control of root rot fungi on okra and sunflower. Pak. J. Bot, 40(3), 1269-1278.
Ehteshamul‐Haque, S. & Ghaffar, A. (1993). Use of rhizobia in the control of root rot diseases of sunflower, okra, soybean and mungbean. Journal of Phytopathology, 138(2), 157-163. https://doi.org/10.1111/j.1439-0434.1993.tb 01372.x
Ellis, M.B. 1971. Dematiaceous Hyphomycetes. Commonwealth Mycological Institute Kew , survey England .608 pp. exudates on fluorescent Pseudomodad sand fungi in solarized soil. Phytopathology, 82, 320 – 327.
El-Saber Batiha, G., Alkazmi, L. M., Wasef, L. G., Beshbishy, A. M., Nadwa, E. H, & Rashwan, E. K. (2020). Syzygium aromaticum L.(Myrtaceae): traditional uses, bioactive chemical constituents, pharmacological and toxicological activities. Biomolecules, 10(2), 202. DOI: 10.3390/biom10020202
Hashim, S. T., Hamza, I. S. & Hassan, M. A. (2013). Appreciation quantitative chemical compounds phenolic extract of the seeds of Syzgium aromaticum and study its inhibitory effect in some food-born pathogenic bacteria. The Iraqi Journal of Veterinary Medicine, 37(2).
Herborne, J. B. (1973). Phytochemical methods. A Guide to Modern Techniques of Plant Analysis, 2, 5-11.
Jimoh, S. O., Arowolo, L. A. & Alabi, K. A. (2017). Phytochemical screening and antimicrobial evaluation of Syzygium aromaticum extract and essential oil. Int. J. Curr. Microbiol. Appl. Sc.i, 6, 4557-4567. https://doi.org/10.20546/ijcmas.2017.607.432
Khoddami, A., Wilkes, M. A. & Roberts, T. H. (2013). Techniques for analysis of plant phenolic compounds. Molecules, 18(2), 2328-2375. doi: 10.3390/molecules18022328.
Kumar, K.P.; Yadav, A.; Srivastava, S.; Paswan, S. & Dutt, A.S. (2012). Recent trends in Indian traditional herbs Syzygium aromaticum and health benefits. J. Pharmacongnocy and Phytochemistry, 1(1), 6-17.
Lavanya, N., & Kelaiya, D. S. (2022). Evaluation of different bio control agents against root rot incidence of castor incited by Macrophomina phaseolina (Tassi) Goid. The Pharma Innovation Journal, 11(8), 955-959.https://www.thepharmajournal.com/archives/2022/vol11issue8/PartL/11-8-22-728.pdf
Le, D. T. & Vu, N. T. (2017). Progress of loop-mediated isothermal amplification technique in molecular diagnosis of plant diseases. Applied Biological Chemistry, 60(2), 169-180. http://dx.doi.org/10.1007%2Fs13765-017-0267-y
Leslie,J.F. & Summerell, B.A. (2006) .The Fusarium Laboratory Manual . Black well Publishing . 388 pp. DOI:10.1002/9780470278376
Mashkor, I. M. A. A. (2015). Evaluation of antioxidant activity of clove (Syzygium aromaticum). Int. J. Chem. Sci, 13(1), 22-30.
Mitscher, L. A., Leu, R. P., Bathala, M. S., Wu, W. N. & Beal, J. L. (1972). Antimicrobial agents from higher plants. I. Introduction, rationale, and methodology. Lloydia, 35(2), 157-166.
Moradi, E., Rakhshandeh, H., Rahimi Baradaran, V., Ghadiri, M., Hasanpour, M., Iranshahi, M. & Askari, V. R. (2023). HPLC/MS characterization of Syzygium aromaticum L. and evaluation of its effects on peritoneal adhesion: Investigating the role of inflammatory cytokines, oxidative factors, and fibrosis and angiogenesis biomarkers. Physiological Reports, 11(2), e15584. doi: 10.14814/phy2.15584.
Najm, M. R, & Sultan, F. I. (2022). Evaluation of Phytochemical Constituents by GC-MS, HPLC and Biological Activity of Peganum Harmala L. Seeds Extract. In IOP Conference Series: Earth and Environmental Science (Vol. 1060, No. 1, p. 012097). IOP Publishing. DOI 10.1088/1755-1315/1060/1/012097
Pitt, J. I. & Hocking, A. D. (2009). Fungi and food spoilage (Vol. 519, p. 388). New York: Springer. https://doi.org/10.1007/978-0-387-92207-2
Razem, M., Ding, Y., Morozova, K., Mazzetto, F. & Scampicchio, M. (2022). Analysis of Phenolic Compounds in Food by Coulometric Array Detector: A Review. Sensors, 22(19), 7498. DOI: 10.3390/s22197498
Sánchez, S., Chamorro, M., Henríquez, J. L., Grez, J., Díaz, I., Santos, B. D. L. & Gambardella, M. (2017). Genetic and biological characterization of Macrophomina phaseolina (Tassi) Goid. causing crown and root rot of strawberry. Chilean journal of Agricultural Research, 77(4), 325-331. http://dx.doi.org/10.4067/S0718-58392017 000400325
Shoko, T.; Soich, T., Megumi, M.M.; Eri, E.; Jun, K. & Michika, W. (1999) Isolation and identification of an antibacterial compound from grape and its application to foods. Noppon Nogeikagaku Kaishi, 73, 125-128. DOI:10.1271/NOGEIKAGAKU1924.73.125Jafeer, K. A. M. M. & Kheirallah, E. A. (2016). Effect of Piper Nigrum fruit and Syzygium aromaticum roses extract on the some of Bacterial and fungal isolate growth. Al-Qadisiyah Journal of Pure Science, 21(2), 36-45
Soto-Vaca, A., Gutierrez, A., Losso, J. N., Xu, Z. & Finley, J. W. (2012). Evolution of phenolic compounds from color and flavor problems to health benefits. Journal of agricultural and food chemistry, 60(27), 6658-6677. https://doi.org/10.1021/jf300861c
Sultan, F.I. (2020). Phytochemical analysis and antibacterial activities of Frankincense of Boswellia serrate. Plant Archives, 20(2): 5219-5226.
Sultan, F.I.; Al-Farha, A.A. & Shaaban, I. (2020A). Separation and identification of some fatty acids and phenolic compounds from Portulaca oleracea L. and study their biological effect on two types of pathogenic bacteria. Asian J. Agric & Biol. AJAB. 8(3): 1-1. DOI: 10.35495/ajab.2020.02.119
Takó M, Kerekes EB, Zambrano C, Kotogán A, Papp T, Krisch J, Vágvölgyi C. (2020). Plant phenolics & phenolic-enriched extracts as antimicrobial agents against food-contaminating microorganisms. Antioxidants (Basel). 9(2),165. doi: 10.3390/antiox9020165. PMID: 32085580; PMCID: PMC7070704.
Yousif, A. A. & Hassan, W. A. (2023). HPLC ANALYSIS AND ANTIFUNGAL ACTIVITY OF SOME PLANT EXTRACTS AGAINST DECAY APPLE FRUITS. Iraqi Journal of Agricultural Sciences, 54(1), 291-302. https://doi.org/10.36103/ijas.v54i1.1702
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Isolation and identification of phenolic compounds from Eugenia caryophyllus and study on its biological effect against Macrophomina phaseolina. (2023). Journal of Applied and Natural Science, 15(4), 1608-1618. https://doi.org/10.31018/jans.v15i4.4880
