Recent Advances in the Bioherbicidal Potential of Tenuazonic Acid, an Alternaria spp. mycotoxin
DOI:
https://doi.org/10.29356/jmcs.v67i3.1994Keywords:
Biological control, fungal metabolites, mycoherbicide, phytotoxinsAbstract
Abstract. This review addresses the current knowledge on the phytotoxic roles of tenuazonic acid and its biosynthesis in Alternaria. We examine recent advances in the biosynthesis of this toxin produced by A. alternata and other fungi; the pathogenicity mechanisms that this molecule displays to exert its bioherbicidal activity; and the risks for human and animal health involved in using tenuazonic acid versus a native mix of toxins produced by A. alternata. Finally, we discuss the potential use of tenuazonic acid versus fungal isolates for agricultural weed control.
Resumen. Esta revisión aborda el estado del arte en el conocimiento acerca de los mecanismos de fitotoxicidad del ácido tenuazónico y su biosíntesis en Alternaria. Se examinan los avances más recientes en la biosíntesis de esta toxina producida por A. alternata y otros hongos; los mecanismos de patogenicidad que esta molécula emplea para ejercer su actividad bioherbicida; así como los riesgos para la salud humana y animal involucrados en el uso de ácido tenuazónico comparado a una mezcla de las toxinas producidas por A. alternata. Finalmente, se discute el uso potencial del ácido tenuazónico versus aislados fúngicos para el control de malezas en la agricultura.
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Bordin, E.; Camargo, A.; Rossetto, V.; Scapini, T.; Modkovski, T.; Weirich, S.; Carezia, C.; Franceschetti, M.; Balem, A.; Golunski, S.; Galon, L.; Fuzinatto, C.; Fongaro, G.; Mossi, A.; Treichel, H. Ind. Biotechnol. 2018, 14, 157-163. DOI: https://doi.org/10.1089/ind.2018.0007
Rai, M.; Zimowska, B.; Shinde, S.; Tres, M. V. J. Appl. Microbiol. Biotechnol. 2021, 105, 3009-3018. DOI: https://doi.org/10.1007/s00253-021-11234-w
Moura, M. S.; Lacerda, J. W. F.; Siqueira, K. A.; Bellete, B. S.; Sousa, P. T.; Dall´Óglio, E. L.; Soares, M. A.; Vieira, L. C. C.; Sampaio, O. M. J. Environ. Sci. Health. 2020, 55, 470-476. DOI: https://doi.org/10.1080/03601234.2020.1721981
Brun, T.; Rabuske, J. E.; Luft, L.; Confortin, T. C.; Todero, I.; Aita, B. C.; Zabot, G. L.; Mazutti, M. A. Environ. Technol. 2020, 43, 2135-2144. DOI: https://doi.org/10.1080/09593330.2020.1867651
Abbas, T.; Zahir, Z. A.; Naveed, M.; Kremer, R. J., in: Advances in Agronomy, Vol. 147, DL Sparks, Ed., Academic Press, 2018, 239-280. DOI: https://doi.org/10.1016/bs.agron.2017.10.005
Bordin, E. R.; Frumi Camargo, A.; Stefanski, F. S.; Scapini, T.; Bonatto, C.; Zanivan, J.; Preczeski, K.; Modkovski, T. A.; Reichert Júnior, F.; Mossi, A. J.; Fongaro, G.; Ramsdorf, W. A.; Treichel, H. Biocatal. Biotransform. 2021, 39, 346-359. DOI: https://doi.org/10.1080/10242422.2020.1833864
Daniel, J. J.; Zabot, G. L.; Tres, M. V.; Harakava, R.; Kuhn, R. C.; Mazutti, M. A. Biocatal. Agric. Biotechnol. 2018, 14, 314-320. DOI: https://doi.org/10.1016/j.bcab.2018.04.001
Prosser, R. S.; Anderson, J. C.; Hanson, M. L.; Solomon, K. R.; Sibley, P. K. Agric., Ecosyst. Environ. 2016, 232, 59-72. DOI: https://doi.org/10.1016/j.agee.2016.07.009
Ferreira, M. I.; Reinhardt, C. F. Afr. J. Agric. Res. 2016, 11, 450-459. DOI: https://doi.org/10.5897/AJAR2015.10580
Souza, A. R. C. d.; Baldoni, D. B.; Lima, J.; Porto, V.; Marcuz, C.; Machado, C.; Ferraz, R. C.; Kuhn, R. C.; Jacques, R. J. S.; Guedes, J. V. C.; Mazutti, M. A. Braz. J. Microbiol. 2017, 48, 101-108. DOI: https://doi.org/10.1016/j.bjm.2016.09.004
Harding, D. P.; Raizada, M. N. Front. Plant Sci. 2015, 6. DOI: https://doi.org/10.3389/fpls.2015.00659
Radhakrishnan, R.; Alqarawi, A. A.; Abd Allah, E. F. Ecotoxicol. Environ. Saf. 2018, 158, 131-138. DOI: https://doi.org/10.1016/j.ecoenv.2018.04.018
Ibrahim, N.; Tawfik, M. Egypt. J. Microbiol. 2019, 54, 117-135.
Meena, M.; Prasad, V.; Upadhyay, R. S. Bull. Environ. Sci. Res. 2016, 5, 1-7.
Charudattan, R.; Dinoor, A. Crop Prot. 2000, 19, 691-695. DOI: https://doi.org/10.1016/S0261-2194(00)00092-2
Abdessemed, N.; Staropoli, A.; Zermane, N.; Vinale F. Pathogens. 2021, 10. DOI: https://doi.org/10.3390/pathogens10111448
Ismaiel, A. A.; Papenbrock, J. Agriculture. 2015, 5, 492-537. DOI: https://doi.org/10.3390/agriculture5030492
Radi, H.; Banaei-Moghaddam, A. Acta Scientific Microbiology. 2020, 3, 62-70. DOI: https://doi.org/10.31080/ASMI.2020.03.0590
Wang, H.; Guo, Y.; Luo, Z.; Gao, L.; Li, R.; Zhang, Y.; Kalaji, H. M.; Qiang, S.; Chen, S. J. Fungi. 2022, 8. DOI: https://doi.org/10.3390/jof8020168
Lou, J.; Fu, L.; Peng, Y.; Zhou, L. Molecules. 2013, 18, 5891-935. DOI: https://doi.org/10.3390/molecules18055891
Howlett, B. J. Curr. Opin. Plant Biol. 2006, 9, 371-5. DOI: https://doi.org/10.1016/j.pbi.2006.05.004
Shi, J.; Zhang, M.; Gao, L.; Yang, Q.; Kalaji, H. M.; Qiang, S.; Strasser, R. J.; Chen, S. Cells. 2021, 10. DOI: https://doi.org/10.3390/cells10051010
Davis, N. D.; Diener, U. L.; Morgan-Jones, G. Appl. Environ. Microbiol. 1977, 34, 155-7. DOI: https://doi.org/10.1128/aem.34.2.155-157.1977
Sun, F.; Cao, X.; Yu, D.; Hu, D.; Yan, Z.; Fan, Y.; Wang, C.; Wu, A. Mol. Plant-Microbe Interact. 2022, 35, 416-427. DOI: https://doi.org/10.1094/MPMI-12-21-0300-R
Rosett, T.; Sankhala, R. H.; Stickings, C. E.; Taylor, M. E.; Thomas, R. Biochem. J. 1957, 67, 390-400. DOI: https://doi.org/10.1042/bj0670390
Wan, Z.; Qiang, S.; Wu, Y. Journal of Beihua University (Natural Science). 2001, 2, 428-430.
Qiang, S.; Wang, L.; Wei, R.; Zhou, B.; Chen, S.; Zhu, Y.; Dong, Y.; An, C. Weed Technol. 2010, 24, 197-201. DOI: https://doi.org/10.1614/WT-D-09-00016.1
Zhou, B.; Qiang, S. J. Agro-Environ. Sci. 2007, 26, 572–576.
Kang, Y.; Feng, H.; Zhang, J.; Chen, S.; Valverde, B. E.; Qiang S. Plant Physiol. Biochem. 2017, 115, 73-82. DOI: https://doi.org/10.1016/j.plaphy.2017.03.002
Chen, S.; Qiang, S. Pestic. Biochem. Physiol. 2017, 143, 252-257. DOI: https://doi.org/10.1016/j.pestbp.2017.01.003
Iwasaki, S.; Muro, H.; Nozoe, S.; Okuda, S.; Sato, Z. Tetrahedron Letters. 1972, 13, 13-16. DOI: https://doi.org/10.1016/S0040-4039(01)84225-8
Steyn, P. S.; Rabie, C. J. Phytochemistry. 1976, 15, 1977-1979. DOI: https://doi.org/10.1016/S0031-9422(00)88860-3
Nishimura, S.; Kohmoto, K. Annu. Rev. Phytopathol. 1983, 21, 87-116. DOI: https://doi.org/10.1146/annurev.py.21.090183.000511
Ebbole, D. J. Annu. Rev. Phytopathol. 2007, 45, 437-456. DOI: https://doi.org/10.1146/annurev.phyto.45.062806.094346
Zhou, B.; Wang, H.; Meng, B.; Wei, R.; Wang, L.; An, C.; Chen, S.; Yang, C.; Qiang, S. Pest Manage. Sci. 2019, 75, 2482-2489. DOI: https://doi.org/10.1002/ps.5402
Templeton, G. E., in: Microbial Toxins, Vol. 6, S Kadis, A Ciegler, and SJ Ajil, Ed., Academic Press, New York/London, 1972, 169-192.
Meena, M.; Samal, S. Toxicol. Rep. 2019, 6, 745-758. DOI: https://doi.org/10.1016/j.toxrep.2019.06.021
Chelkowski, J.; Visconti, A., Elsevier Science, Amsterdam, London, New York, Tokyo. 1992, 449-541.
Zonno, M. C.; Vurro, M. Weed Research. 1999, 39, 15-20. DOI: https://doi.org/10.1046/j.1365-3180.1999.00119.x
Janardhanan, K. K.; Husain, A. J. Phytopathol. 1984, 111, 305-311. DOI: https://doi.org/10.1111/j.1439-0434.1984.tb00774.x
Apel, K.; Hirt, H. Annu. Rev. Plant Biol. 2004, 55, 373-399. DOI: https://doi.org/10.1146/annurev.arplant.55.031903.141701
Laloi, C.; Apel, K.; Danon, A. Curr. Opin. Plant Biol. 2004, 7, 323-328. DOI: https://doi.org/10.1016/j.pbi.2004.03.005
Chen, S.; Yin, C.; Qiang, S.; Zhou, F.; Dai X. Biochim. Biophys. Acta. 2010, 1797, 391-405. DOI: https://doi.org/10.1016/j.bbabio.2009.12.007
Gatenbeck, S.; Sierankiewicz, J. Antimicrob Agents Chemother. 1973, 3, 308-9. DOI: https://doi.org/10.1128/AAC.3.2.308
Miller, F. A.; Rightsel, W. A.; Sloan, B. J.; Ehrlich, J.; French, J. C.; Bartz, Q. R.; Dixon, G. J. Nature. 1963, 200, 1338-1339. DOI: https://doi.org/10.1038/2001338a0
Nukina, M.; Saito, T. Biosci., Biotechnol., Biochem. 1992, 56, 1314-1315. DOI: https://doi.org/10.1271/bbb.56.1314
Stickings, C. E. Biochem. J. 1959, 72, 332-40. DOI: https://doi.org/10.1042/bj0720332
Stickings, C. E.; Townsend, R. J. Biochem. J. 1961, 78, 412-418. DOI: https://doi.org/10.1042/bj0780412
Collemare, J.; Billard, A.; Böhnert, H. U.; Lebrun, M.-H. Mycol. Res. 2008, 112, 207-215. DOI: https://doi.org/10.1016/j.mycres.2007.08.003
Royles, B. J. L. Chemical Reviews. 1995, 95, 1981-2001. DOI: https://doi.org/10.1021/cr00038a009
Yun, C.-S.; Motoyama, T.; Osada, H. Nat. Commun. 2015, 6, 8758. DOI: https://doi.org/10.1038/ncomms9758
Yun, C. S.; Nishimoto, K.; Motoyama, T.; Shimizu, T.; Hino, T.; Dohmae, N.; Nagano, S.; Osada, H. J. Biol. Chem. 2020, 295, 11602-11612. DOI: https://doi.org/10.1074/jbc.RA120.013105
Mo, X.; Gulder, T. A. M. Nat. Prod. Rep. 2021, 38, 1555-1566. DOI: https://doi.org/10.1039/D0NP00099J
Chen, S.; Zhou, F.; Yin, C.; Strasser, R. J.; Yang, C.; Qiang, S. Environ. Exp. Bot. 2011, 73, 31-41. DOI: https://doi.org/10.1016/j.envexpbot.2011.08.005
Chen, S.; Yin, C.; Strasser, R. J.; Govindjee; Yang, C.; Qiang, S. Plant Physiol. Biochem. 2012, 52, 38-51. DOI: https://doi.org/10.1016/j.plaphy.2011.11.004
Qin, J. C.; Zhang, Y. M.; Hu, L.; Ma, Y. T.; Gao, J. M. Nat. Prod. Commun. 2009, 4, 1473-6.
Lebrun, M. H.; Nicolas, L.; Boutar, M.; Gaudemer, F.; Ranomenjanahary, S.; Gaudemer, A. Phytochemistry. 1988, 27, 77-84. DOI: https://doi.org/10.1016/0031-9422(88)80594-6
Bok, J. W.; Keller, N. P. Eukaryot Cell. 2004, 3, 527-35. DOI: https://doi.org/10.1128/EC.3.2.527-535.2004
Yun, C.-S.; Motoyama, T.; Osada, H. ACS Chem. Biol. 2017, 12, 2270-2274. DOI: https://doi.org/10.1021/acschembio.7b00353
Pero, R. W.; Posner, H.; Blois, M.; Harvan, D.; Spalding, J. W. Environ. Health Perspect. 1973, 4, 87-94. DOI: https://doi.org/10.1289/ehp.730487
EFSA. EFSA J. 2011, 9, 2407. DOI: https://doi.org/10.2903/j.efsa.2011.2407. DOI: https://doi.org/10.2903/j.efsa.2011.2407
EFSA; Arcella, D.; Eskola, M.; Gómez Ruiz, J. A. EFSA J. 2016, 14, e04654. DOI: https://doi.org/10.2903/j.efsa.2016.4654. DOI: https://doi.org/10.2903/j.efsa.2016.4654
Fehr, M.; Pahlke, G.; Fritz, J.; Christensen, M. O.; Boege, F.; Altemöller, M.; Podlech, J.; Marko, D. Mol. Nutr. Food Res. 2009, 53, 441-451. DOI: https://doi.org/10.1002/mnfr.200700379
Tiessen, C.; Fehr, M.; Schwarz, C.; Baechler, S.; Domnanich, K.; Böttler, U.; Pahlke, G.; Marko, D. Toxicol. Lett. 2013, 216, 23-30. DOI: https://doi.org/10.1016/j.toxlet.2012.11.005
Aichinger, G.; Beisl, J.; Marko, D. Mol. Nutr. Food Res. 2017, 61, 1600462. DOI: https://doi.org/10.1002/mnfr.201600462
Fleck, S. C.; Burkhardt, B.; Pfeiffer, E.; Metzler, M. Toxicol. Lett. 2012, 214, 27-32. DOI: https://doi.org/10.1016/j.toxlet.2012.08.003
Schwarz, C.; Tiessen, C.; Kreutzer, M.; Stark, T.; Hofmann, T.; Marko, D. Arch. Toxicol. 2012, 86, 1911-1925. DOI: https://doi.org/10.1007/s00204-012-0958-4
Tiessen, C.; Gehrke, H.; Kropat, C.; Schwarz, C.; Bächler, S.; Fehr, M.; Pahlke, G.; Marko, D. World Mycotoxin J. 2013, 6, 233-244. DOI: https://doi.org/10.3920/WMJ2013.1592
Aichinger, G.; Del Favero, G.; Warth, B.; Marko, D. Compr. Rev. Food Sci. Food Saf. 2021, 20, 4390-4406. DOI: https://doi.org/10.1111/1541-4337.12803
Roberts, J.; Florentine, S.; Fernando, W. G. D.; Tennakoon, K. U. Plants. 2022, 11, 2242. DOI: https://doi.org/10.3390/plants11172242
https://www.dof.gob.mx/nota_detalle.php?codigo=5609365, accessed in February 2023
Dalinova, A. A.; Salimova, D. R.; Berestetskiy, A. O. Appl. Biochem. Microbiol. 2020, 56, 256-272. DOI: https://doi.org/10.1134/S0003683820030023
Triolet, M.; Guillemin, J.-P.; Andre, O.; Steinberg, C. Weed Res. 2019, 60, 60-77. DOI: https://doi.org/10.1111/wre.12389
Hasan, M.; Ahmad-Hamdani, M. S.; Rosli, A. M.; Hamdan, H. Plants. 2021, 10, 1212. DOI: https://doi.org/10.3390/plants10061212
Hoagland, R. E.; Boyette, C. D. J. Fungi. 2021, 7, 1032. DOI: https://doi.org/10.3390/jof7121032
Duke, S. O.; Pan, Z.; Bajsa-Hirschel, J.; Boyette, C. D. Adv. Weed Sci. 2022, 40. DOI: https://doi.org/10.51694/AdvWeedSci/2022;40:seventy-five003
Siddiqui, I.; Bajwa, R. Int. J. Agric. Biol. 2008, 10, 722-724.
Siddiqui, I.; Bajwa, R.; Javaid, D. A. Afr. J. Biotechnol. 2010, 9, 8308-8312.
Babu, R. M.; Sajeena, A.; Seetharaman, K. Crop Protection. 2003, 22, 1005-1013. DOI: https://doi.org/10.1016/S0261-2194(03)00115-7
Dagno, K.; Lahlali, R.; Diourté, M.; Jijakli, M. H. Biotechnol., Agron., Soc. Environ. 2012, 16, 360-368.
Singh, A. K.; Pandey, A. K. Int. J. Plant Environ. 2022, 8, 44-51. DOI: https://doi.org/10.18811/ijpen.v8i01.05
Cordeau, S.; Triolet, M.; Wayman, S.; Steinberg, C.; Guillemin, J.-P. Crop Prot. 2016, 87, 44-49. DOI: https://doi.org/10.1016/j.cropro.2016.04.016
Kausar, T.; Jabeen, K.; Javaid, A.; Iqbal, S. Adv. Weed Sci. 2022, 40. DOI: https://doi.org/10.51694/AdvWeedSci/2022;40:00002
Sands, D. C.; Pilgeram, A. L. Pest. Manag. Sci. 2009, 65, 581-587. DOI: https://doi.org/10.1002/ps.1739
Suckling, D. M. Biol. Control. 2013, 66, 27-32. DOI: https://doi.org/10.1016/j.biocontrol.2013.02.009


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