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 JACEN  Vol.8 No.3 , August 2019
A Phytotoxic and Antifungal Metabolite (Pyrichalasin H) from a Fungus Infecting Brachiaria eruciformis (Signal Grass)
Abstract: Brachiaria eruciformis (sm.) Griseb, locally known as “signal grass”, is a common weed in lawns and turfs in Mississippi, USA. During late spring and early summer months, leaves of B. eruciformis are infected with a fungus causing necrosis. The infected leaves ultimately turn brown and wither. As part of our search for potential new natural product-based agrochemicals, we studied this plant pathogen in order to investigate phytotoxic and fungitoxic metabolites produced by the fungus. The causative fungus was isolated from an infected leaf of B. eruciformis, cultured in potato dextrose agar plates and identified via molecular techniques as Pyricularia grisea. A phytotoxic compound was isolated from Czapek-Dox broth liquid culture medium and identified as pyrichalasin H by spectroscopic techniques. Pyrichalasin H was toxic to the fungal plant pathogen Colletotrichum fragariae in a TLC bioautography assay and phytotoxic to two monocot and one dicot plants. This is the first report of antifungal activity of pyrichalasin H against phytopathogens. Pyrichalasin H isolated from Pyricularia grisea, a pathogen infecting B. eruciformis (signal grass) was shown to be phytotoxic and fungicidal to Colletotrichum fragariae.
Cite this paper: Meepagala, K. , Clausen, B. , Johnson, R. , Wedge, D. and Duke, S. (2019) A Phytotoxic and Antifungal Metabolite (Pyrichalasin H) from a Fungus Infecting Brachiaria eruciformis (Signal Grass). Journal of Agricultural Chemistry and Environment, 8, 115-128. doi: 10.4236/jacen.2019.83010.
References

[1]   Monciardini, P., Iorio, M., Maffioli, S., Sosio, M. and Donadio, S. (2014) Discovering New Bioactive Molecules from Microbial Sources. Microbial Biotechnology, 7, 209-220.
https://doi.org/10.1111/1751-7915.12123

[2]   Macheleidt, J., Mattern, D.J., Fischer, J., Netzker, T., Weber, J., Schroeckh, V., Valiante, V. and Brakhage, A.A. (2016) Regulation and Role of Fungal Secondary Metabolites. Annual Review of Genetics, 50, 371-392.
https://doi.org/10.1146/annurev-genet-120215-035203

[3]   Ogorek, R. (2016) Enzymatic Activity of Potential Fungal Plant Pathogens and the Effect of Their Culture Filtrates on Seed Germination and Seedling Growth of Garden Cress (Lepidium sativum L.). European Journal of Plant Pathology, 145, 469-481.
https://doi.org/10.1007/s10658-016-0860-7

[4]   Kim, W., Park, J.-J., Dugan, F.M., Peever, T.L., Gang, D.R., Vandemark, G. and Chen, W. (2017) Production of the Antibiotic Secondary Metabolite Solanapyrone A by the Fungal Plant Pathogen Ascochytarabiei during Fruiting Body Formation in Saprobic Growth. Environmental Microbiology, 19, 1822-1835.
https://doi.org/10.1111/1462-2920.13673

[5]   Duke, S.O. and Dayan, F.E. (2018) Herbicides. John Wiley & Sons, Chichester.
https://doi.org/10.1002/9780470015902.a0025264

[6]   Dayan, F.E., Cantrell, C.L. and Duke, S.O. (2009) Natural Products in Crop Protection. Bioorganic & Medicinal Chemistry, 17, 4022-4034.
https://doi.org/10.1016/j.bmc.2009.01.046

[7]   Heap, I. and Duke, S.O. (2018) Overview of Glyphosate-Resistant Weeds Worldwide. Pest Management Science, 74, 1040-1049.
https://doi.org/10.1002/ps.4760

[8]   Sparks, T.C., Hahn, D.R. and Garizi, N.V. (2017) Natural Products, Their Derivatives, Mimics and Synthetic Equivalents: Role in Agrochemical Discovery. Pest Management Science, 74, 700-715.
https://doi.org/10.1002/ps.4458

[9]   Dayan, F.E., Romagni, J.G. and Duke, S.O. (2000) Investigating the Mode of Action of Natural Phytotoxins. Journal of Chemical Ecology, 2, 2079-2094.
https://doi.org/10.1023/A:1005512331061

[10]   Michel, A., Johnson, R.D., Duke, S.O. and Scheffler, B.E. (2004) Dose-Response Relationships between Herbicides with Different Modes of Action and Growth of Lemnapaucicostata—An Improved Ecotoxicological Method. Environmental Toxicology and Chemistry, 23, 1074-1079.
https://doi.org/10.1897/03-256

[11]   Duke, S.O. and Kenyon, W.H. (1993) Peroxidizing Activity Determined by Cellular Leakage. In: Boger, P. and Sandman, G., Eds., Target Assays for Modern Herbicides and Related Phytotoxic Compounds, Lewis, Boca Raton, 61-66.

[12]   Dayan, F.E. and Duke, S.O. (2010) Protoporphyrinogen Oxidase-Inhibiting Herbicides. In: Krieger, R.I., Doull, J., Hodgson, E., Maibach, H., Reiter, L., Ross, J., Slikker, W.J. and Van Hemmon, J., Eds., Haye’s Handbook of Pesticide Toxicology, 3rd Edition, Vol. 2, Academic Press, Elsevier, San Diego, 1733-1751.
https://doi.org/10.1016/B978-0-12-374367-1.00081-1

[13]   Hiscox, J.D. and Israelstam, G.F. (1979) A Method for the Extraction of Chlorophyll from Leaf Tissue without Maceration. Canadian Journal of Botany, 57, 1332-1334.
https://doi.org/10.1139/b79-163

[14]   Wedge, D.E. and Nagle, D.G. (2000) A New 2D TLC Bioautography Method for the Discovery of Novel Antifungal Agents to Control Plant Pathogens. Journal of Natural Products, 63, 1050-1054.
https://doi.org/10.1021/np990628r

[15]   Oliva, A., Meepagala, K.M., Wedge, D.E., Harries, D., Hale, A.L., Aliotta, G. and Duke, S.O. (2003) Natural Fungicides from Ruta graveolens L. Leaves, Including a New Quinolone Alkaloid. Journal of Agricultural and Food Chemistry, 51, 890-896.
https://doi.org/10.1021/jf0259361

[16]   Meepagala, K.M., Schrader, K.K., Burandt, C.L., Wedge, D.E. and Duke, S.O. (2010) New Class of Algicidal Compounds and Fungicidal Activities Derived from a Chromene Amide of Amyris texana. Journal of Agricultural and Food Chemistry, 58, 9476-9482.
https://doi.org/10.1021/jf101626g

[17]   Scherlach, K., Boettger, D., Remme, N. and Hertweck, C. (2010) The Chemistry and Biology of Cytochalasans. Natural Product Reports, 27, 869-886.
https://doi.org/10.1039/b903913a

[18]   Ismaiel, A.A. and Papenbrock, J. (2015) Fungal Phytotoxins with Potential Herbicidal Activity: Chemical and Biological Characterization. Agriculture, 5, 492-537.
https://doi.org/10.3390/agriculture5030492

[19]   Cimmino, A., Masi, M., Evidente, M., Superchi, S. and Evidente, A. (2015) Fungal Phytotoxins with Potential Herbicidal Activity: Chemical and Biological Characterization. Natural Product Reports, 32, 1629-1653.
https://doi.org/10.1039/C5NP00081E

[20]   Tsurushima, T., Don, L.D., Kawashima, K., Murakami, J., Nakayashiki, H., Tosa, Y. and Mayama, S. (2005) Pyrichalasin H Production and Pathogenicity of Digitaria-Specific Isolates of Pyriculariagrisea. Molecular Plant Pathology, 6, 605-613.
https://doi.org/10.1111/j.1364-3703.2005.00309.x

[21]   Nukina, M. (1987) Pyrichalasin H, a New Phytotoxic Metabolite Belonging to the Cytochalasansfrom Pyriculariagrisea (Cooke) Saccardo. Agricultural and Biological Chemistry, 51, 2625-2628.
https://doi.org/10.1271/bbb1961.51.2625

[22]   Sanmathi, K.R.P., Shanthala, L., Anikumar, T.B. and Sudharshana, L. (2006) Phytotoxins from Pyriculariagrisea and Their Effect on Finger Millet. Journal of Plant Biochemistry and Biotechnology, 15, 63-66.
https://doi.org/10.1007/BF03321905

[23]   Hirose, T., Izawa,Y., Koyama, K., Natori, S., Iida, K., Yahara, I., Shimaoka, S. and Maruyama (1990) The Effects of New Cytochalasins from Phomopsis sp. and the Derivatives on Cellular Structure and Actin Polymerization. Chemical and Pharmaceutical Bulletin, 38, 971-974.
https://doi.org/10.1248/cpb.38.971

[24]   Yahara, I., Harada, F., Sekita, S., et al. (1982) Correlation between Effects of 24 Different Cytochalas Ins on Cellular Structures and Cellular Events and Those on Actin in Vitro. The Journal of Cell Biology, 92, 69-78.
https://doi.org/10.1083/jcb.92.1.69

[25]   Cutler, H.G., Cutler, S.J. and Matesic, D. (2004) Mode of Action of Phytotoxic Fungal Metabolites. In: Macias, F.A., Galindo, J.C.G., Molinillo, J.M.G. and Cutler, H.G., Eds., Allelopathy: Chemistry and Mode of Action of Allelochemicals, CRC Press, Boca Raton, 253-270.
https://doi.org/10.1201/9780203492789.ch13

 
 
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