Abstract
More than 300 metabolites of fungi of the genera Alternaria have been reported in the last few decades; some of them display phytotoxic, antibiotic, antifungal, and antiprotozoal activity. This review synthesizes the current information on the structure, biological activity, and possible application of Alternaria metabolites in plant protection, pharmacology, and chemotaxonomy. Some Alternaria fungi are suggested as mycoherbicides. The toxicology of application of the Alternaria fungi as mycoherbicides is discussed.
Similar content being viewed by others
REFERENCES
Lawrence, D., Rotondo, F., and Gannibal, P., Mycol. Prog., 2016, vol. 15, no. 3, pp. 1–22.
Woudenberg, J.H.C., Seidl, M.F., Groenewald, J.Z., de Vries, M., Stielow, J.B., Thomma, B.P.H.J., and Crous, P.W., Stud. Mycol., 2015, vol. 82, pp. 1–21.
Gannibal, Ph.B., Mycotaxon, 2018, vol. 133, no. 1, pp. 37–43.
Thomma, H.J., Mol. Plant Pathol., 2003, vol. 4, no. 2, pp. 225–236.
Bannon, J.S., Am. J. Altern. Agr., 1988, vol. 3, nos. 2–3, pp. 73–76.
Shabana, Y.M., Charudattan, R., and Elwakil, M.A., Biol. Control., 1995, vol. 5, no. 2, pp. 136–144.
Green, S. and Bailey, K.L., Biol. Control., 2000, vol. 19, no. 2, pp. 167–174.
Kaur, J. and Aggarwal, N.K., Crop Prot., 2015, vol. 4, pp. 719–726.
Lou, J., Peng, Y., Fu, L., and Zhou, L., Molecules, 2013, vol. 18, no. 5, pp. P. 5891–5935.
Berestetskii, A.O., Dalinova, A.A., and Volosatova, N.S., Appl. Biochem. Microbiol., 2019, vol. 55, no. 3, pp. 271–281.
Duke, S.O., Owens, D.K., and Dayan, F.E., Weed Control: Sustainability, Hazards, and Risks in Cropping Systems Worldwide, Korres, N.E., Burgos, N.R., and Duke, S.O., Eds., Boca Raton, FL: CRC Press, 2019.
Streit, E., Schwab, C., Sulyok, M., Naehrer, K., Krska, R., and Schatzmayr, G., Toxins, 2013, vol. 5, no. 3, pp. 504–523.
Pero, R.W., Posner, H., Blois, M., Harvan, D., and Spalding, J.W., Environ. Health Perspect., 1973, vol. 4, pp. 87–94.
Ostry, V., World Mycotoxin J., 2008, vol. 1, no. 2, pp. 175–188.
Meronuck, R.A., Steele, J.A., Mirocha, C.J., and Christensen, C.M., Appl. Microbiol., 1972, vol. 23, no. 3, pp. 613–617.
Pinto, V.E.F. and Patriarca, A., Mycotoxigenic Fungi: Methods and Protocols, Moretti, A. and Susca, A., Eds., New York: Springer Science+Business Media LLC, 2017.
Phuwapraisirisana, P., Nat. Prod. Res., 2009, vol. 23, no. 12, pp. 1063–1071.
Vaquera, S., Patriarca, A., and Pinto, V.F., Int. J. Food Microbiol., 2016, vol. 219, pp. 44–49.
Tian, J., Fu, L., Zhang, Z., Dong, X., Xu, D., Mao, Z., et al., Nat. Prod. Res., 2016, vol. 31, no. 4, pp. 387–396.
Griffin, G.F. and Chu, F.S., Appl. Environ. Microbiol., 1983, vol. 46, no. 6, pp. 1420–1422.
Bottalico, A. and Logrieco, A., in Mycotoxins in Agriculture and Food Safety, Sinha, K.K. and Bhatnagar, D., Eds., New York: Marcel Dekker Inc., 1998, pp. 65–108.
Brugger, E-M., Wagner, J., Schumacher, D.M., Koch, K., Podlech, J., Metzler, M., and Lehmann, L., Toxicol. Lett., 2006, vol. 164, no. 3, pp. 221–230.
Solhaug, A., Eriksen, G.S., and Holme, J.A., Basic Clin. Pharmacol. Toxicol., 2016, vol. 119, no. 6, pp. 533–539.
Liu, G.T., Qian, Y.Z., Zhang, P., Dong, W.H., Qi, Y.M., and Guo, H.T., Chin. Med. J., 1992, vol. 105, no. 5, pp. 394–400.
Bensassi, F., Gallerne, C., Sharaf, El., and Dein, O., Toxicol. In Vitro, 2012, vol. 26, no. 6, pp. 915–923.
Fehr, M., Pahlke, G., Fritz, J., Christensen, M.O., Boege, F., Altemoller, M., Podlech, J., and Marko, D., Mol. Nutr. Food Res., 2009, vol. 53, no. 4, pp. 441–451.
Fernandez-Blanco, C., Juan-García, A., Juan, C., Font, G., and Ruiz, M.-J., Food Chem. Toxicol., 2016, vol. 88, pp. 32–39.
Grover, S. and Lawrence, C.B., Int. J. Mol. Sci., 2017, vol. 18, no. 7, p. 1577. https://doi.org/10.3390/ijms18071577
Tiemann, U., Tomek, W., Schneider, F., Müller, M., Pöhland, R., and Vanselow, J., Toxicol. Lett., 2009, vol. 86, pp. 139–145.
Dellafiora, L., Warth, B., Schmidt, V., Del Favero, G., Mikula, H., Fröhlich, J., and Marko, D., Food Chem., 2018, vol. 248, pp. 253–261.
Stack, M.E. and Prival, M.J., Appl. Environ. Microbiol., 1986, vol. 52, no. 4, pp. 718–722.
Fleck, S.C., Burkhardt, B., Pfeiffer, E., and Metzler, M., Toxicol. Lett., 2012, vol. 214, no. 1, pp. 27– 32.
Schwarz, C., Tiessen, C., Kreutzer, M., Stark, T., Hofmann, T., and Marko, D., Arch. Toxicol., 2012, vol. 86, no. 12, pp. 1911–1925.
Del Favero, G., Zaharescu, R., and Marko, D., Arch. Toxicol., 2018, vol. 92, no. 12, pp. 3535–3547.
Boutin, B., Peeler, J., and Twedt, R., J. Toxicol. Environ. Health, 1989, vol. 26, no. 1, pp. 75–81.
Sedova, I.B., Kiseleva, M.G., Chalyi, Z.A., Aksenov, I.V., and Zakharova, L.P., Usp. Med. Mikol., 2018, vol. 19, pp. 329–330.
Gotthardt, M., Asam, S., Gunkel, K., Moghaddam, A.F., Baumann, E., Kietz, R., and Rychlik, M., Front. Microbiol., 2019, vol. 10, p. 109. https://doi.org/10.3389/fmicb.2019.00109
European Food Safety Authority (EFSA), EFSA J., 2016, vol. 14, no. 12. e04643. https://doi.org/10.2903/j.efsa.2016.4643
Asam, S., Habler, K., and Rychlik, M., Anal. Bioanal. Chem., 2013, vol. 405, no. 12, pp. 4149–4158.
Fliszár-Nyul, E., Lemli, B., Kunsági-Máté, S., Dellafiora, L., Dall’Asta, C., Cruciani, G., and Poór, M., Int. J. Mol. Sci., 2019, vol. 20, no. 9, p. 2352. https://doi.org/10.3390/ijms20092352
Schuchardt, S., Ziemann, C., and Hansen, T., EFSA Support.Publ., 2014, vol. 11, no. 11, p. 679E. https://doi.org/10.2903/sp.efsa.2014.EN-679
Zwickel, T., Kahl, S., Klaffke, H., Rychlik, M., and Muller, M., Toxins, 2016, vol. 8, no. 11, p. 344.
Vejdovszky, K., Schmidt, V., Warth, B., and Marko, D., Mol. Nutr. Food Res., 2016, vol. 61, no. 3. 1600526. https://doi.org/10.1002/mnfr.201600526
Vejdovszky, K., Sack, M., Jarolim, K., Aichinger, G., Somoza, M.M., and Marko, D., Toxicol. Lett., 2017, vol. 267, pp. 45–52.
Escrivá, L., Oueslati, S., Font, G., and Manyes, L., J. Food Qual, 2017, pp. 1–20. https://doi.org/10.1155/2017/1569748
Puntscher, H., Kutt, M.-L., Skrinjar, P., Mikula, H., Podlech, J., Fröhlich, J., and Warth, B., Anal. Bioanal. Chem., 2018, vol. 410, no. 18, pp. 4481–4494.
Myresiotis, C.K., Testempasis, S., Vryzas, Z., Karaoglanidis, G.S., and Papadopoulou-Mourkidou, E., Food Chem., 2015, vol. 182, pp. 81–88.
Amelin, V.G., Karaseva, N.M., and Tret’yakov, A.V., Zh. Anal. Khim., 2013, vol. 68, no. 3, pp. 212–223.
Berthiller, F., Crews, C., Dall’Asta, C., Saeger, S.D., Haesaert, G., Karlovsky, P., and Stroka, J., Mol. Nutr. Food Res., 2012, vol. 57, no. 1, pp. 165–186.
Puntscher, H., Cobankovic, I., Marko, D., and Warth, B., Food Control., 2019, vol. 102, pp. 157–165.
Puntscher, H., Hankele, S., Tillmann, K., Attakpah, E., Braun, D., Kutt, M.L., Del Favero, G., Aichinger, G., Pahlke, G., Hoger, H., Marko, D., and Warth, B., Toxicol. Lett., 2019, vol. 301, pp. 168-178.
Lee, H.B., Patriarca, A., and Magan, N., Mycobiology, 2015, vol. 43, no. 2, pp. 93–106.
Noser, J., Schneider, P., Rother, M., and Schmutz, H., Mycotoxin Res., 2011, vol. 27, no. 4, pp. 265–271.
Burkin, A.A. and Kononenko, G.P., Appl. Biochem. Microbiol., 2011, vol. 47, no. 1, pp. 72–76.
Dzhatdoeva, A.A., Selimov, R.N., Gracheva, T.S., Metal’nikov, P.S., and Komarov, A.A., Usp. Med. Mikol., 2018, vol. 19, pp. 297–298.
Selimov, R.N., Dzhatdoeva, A.A., Metal’nikov, P.S., and Komarov, A.A., Veterinariya, 2017, no. 12, pp. 53–57.
Prendes, L.P., Fontana, A.R., Merin, M.G., D´ Amario Fernández, A., Bottini, R., Ramirez, M.L., and Morata de Ambrosini, V.I., Food Sci. Nutr., 2018, vol. 6, no. 3, pp. 523–531.
Walravens, J., Mikula, H., Rychlik, M., Asam, S., Devos, T., Njumbe, EdiageE., and De Saeger, S., J. Agr. Food Chem., 2016, vol. 64, no. 24, pp. 5101–5109.
Ramires, F., Masiello, M., Somma, S., Villani, A., Susca, A., Logrieco, A., and Moretti, A., Toxins, 2018, vol. 10, no. 11, p. 472. https://doi.org/10.3390/toxins10110472
Puntscher, H., Marko, D., and Warth, B., Front. Nutrit., 2019, vol. 6, p. 92.
Tan, X., Zhang, X., Yu, M., Yu, Y., Guo, Z., Gong, T., and Ding, G., Phytochemistry, 2019, vol. 164, pp. 154–161.
Brase, S., Glaser, F., Kramer, C.S., Linder, S., Linsenmeier, A.M., Masters, K.S., Meister, A.C., Ruff, B.M., and Zhong, S., Prog. Chem. Org. Nat. Prod., 2013, vol. 97, pp. 1–300.
Möbius, N. and Hertweck, C., Curr. Opin. Plant Biol., 2009, vol. 12, no. 4, pp. 390–398.
Mitchell, R.E., Annu. Rev. Phytopalhol., 1984, vol. 22, pp. 215–245.
Berestetskii, A.O., Chistyi, L.S., and Mironenko, N.V., Mikol. Fitopatol., 2018, vol. 52, no. 3, pp. 196–207.
Akimitsu, K., Tsuge, T., Kodama, M., Yamamoto, M., and Otani, H., J. Gen. Plant. Pathol., 2014, vol. 80, no. 2, pp. 109–122.
Tsuge, T., Harimoto, Y., Akimitsu, K., Ohtani, K., Kodama, M., Akagi, Y., Egusa, M., Yamamoto, M., and Otani, H., FEMS Microbiol. Rev., 2013, vol. 37, no. 1, pp. 44–66.
Park, P., Nishimura, S., Kohmoto, K., Otani, H., and Tsujimoto, K., Can. J. Bot., 1981, vol. 59, no. 3, pp. 301–310.
Yamagishi, D., Akamatsu, H., Otani, H., and Kodama, M., J. Gen. Plant. Pathol., 2006, vol. 72, no. 5, pp. 323–327.
Friesen, T.L., Faris, J.D., Solomon, P.S., and Oliver, R.P., Cell. Microbiol., 2008, vol. 10, no. 7, pp. 1421–1428.
Ueno, T., Nakashima, T., Hayashi, Y., and Fukami, H., Agr. Biol. Chem., 1975, vol. 39, no. 5, pp. 1115–1122.
Nakashima, T., Ueno, T., Fukami, H., Taga, T., Masuda, H., Osaki, K., Otani, H., Kohmoto, K., and Nishimura, S., Agr. Biol. Chem., 1985, vol. 49, no. 3, pp. 807–815.
Nakatsuka, S., Ueda, K., Goto, T., Yamamoto, M., Nishimura, S., and Kohmoto, K., Tetrahedron Lett., 1986, vol. 27, no. 24, pp. 2753–2756.
Itoh, Y., Kohmoto, K., Shimomura, N., Otani, H., Kodama, M., and Nakatsuka, S.A., Ann. Phytopath. Soc. Japan, 1993, vol. 59, no. 4, pp. 416–427.
Gardner, J.M., Konoa, Y., Tatumb, J.H., Suzukia, Y., and Takeuchia, S., Phytochemistry, 1985, vol. 24, no. 12, pp. 2861–2867.
Clouse, S.D., Martensen, A.N., and Gilchrist, D.G., J. Chromatogr., 1985, vol. 350, pp. 255–263.
Ohtani, K., Yamamoto, H., and Akimitsu, K., Proc. Natl. Acad. Sci. U. S. A., 2002, vol. 99, no. 4, pp. 2439–2444.
Gannibal, F.B., Bil’der, I.V., and Uli-Mattila, T., Mik-ol. Fitopatol., 2008, vol. 42, no. 1, pp. 18–25.
Prieto, K.R., Medeiros, L.S., Isidoro, M.M., Toffano, L., Silva, M.F.G.F., Da Fernandes, J.B., and Machado, M.A., J. Braz. Chem. Soc., 2016, vol. 27, no. 8, pp. 1493–1505.
Garganese, F., Schena, L., Siciliano, I., Prigigallo, M.I., Spadaro, D., De Grassi, A., and Sanzani, S.M., PLoS One, 2016, vol. 11, no. 9. e0163255. https://doi.org/10.1371/journal.pone.0163255
Meena, M. and Samal, S., Toxicol. Rep., 2019, vol. 6, pp. 745–758.
Brian, P.W., Curtis, P.J., Hemming, H.G., Unwin, C.H., and Wright, G.M., Nature, 1949, vol. 164, no. 4169, p. 534. https://doi.org/10.1038/164534a0
Langsdorf, G., Fururchi, N., Doke, N., and Nishimura, S., J. Phytopathol., 1990, vol. 128, no. 4, pp. 271–282.
Brian, P.W., Elson, G.W., Hemming, H.G., and Wright, J.M., Ann. Appl. Biol., 1952, vol. 39, no. 3, pp. 308–321.
Furuichi, N., Nishimura, S., and Langsdorf, G., Ann. Phytopath. Soc. Japan, 1992, vol. 58, pp. 1–7.
Bessadat, N., Berruyer, R., Hamon, B., Bataille-Simoneau, N., Benichou, S., Kihal, M., and Simoneau, P., Eur. J. Plant Pathol., 2016, vol. 148, no. 1, pp. 181–197.
Stoessl, A., Chem. Commun., 1967, no. 7, pp. 307–308.
Haraguchi, H., Abo, T., Fukuda, A., Okamura, N., and Yagi, A., Phytochemistry, 1996, vol. 43, no. 5, pp. 989–992.
Ichihara, A., Tazaki, H., and Sakamura, S., Tetrahedron Lett., 1983, vol. 24, no. 48, pp. 5373–5376.
Hohl, B., Weidemann, C., Hohl, U., and Barz, W., J. Phytopathol., 1991, vol. 132, no. 3, pp. 193–206.
Kim, W., Park, C.-M., Park, J.-J., Akamatsu, H.O., Peever, T.L., Xian, M., Gang, D.R., Vandemark, G., and Chen, W., MPMI, 2015, vol. 28, no. 4, pp. 482–496.
Liebermann, B., Ellinger, R., and Ihn, W., J. Phytopathol., 1994, vol. 140, pp. 385–388.
Liebermann, B., Nussbaum, R.-P., and Gunther, W., Phytochemistry, 2000, vol. 55, no. 8, pp. 987–992.
Ayer, W.A. and Pena-Rodriguez, L.M., J. Nat. Prod., 1987, vol. 50, no. 3, pp. 400–407.
Parada, R.Y., Oka, K., Yamagishi, D., Kodama, M., and Otani, H., Physiol. Mol. Plant, 2007, vol. 71, nos. 1–3, pp. 48–54.
Pedras, M.S., Biesenthal, C.J., and Zaharia, I.L., Plant Sci., 2000, vol. 156, no. 2, pp. 185–192.
Ibrahim, A.A. and Asker, M.S., Aust. J. Basic Appl. Sci., 2012, vol. 6, no. 5, pp. 284–288.
Butt, T.M., Hadj, N.B.E., Skrobek, A., Ravensberg, W.J., Wang, C., Lange, C.M., and Dudley, E., Rapid Commun. Mass Spectrom., 2009, vol. 23, no. 10, pp. 1426–1434.
Pedras, M.S. and Khallaf, I., Phytochemistry, 2012, vol. 77, pp. 129–139.
Gloer, J.B., Poch, G.K., Short, D.M., and McCloskey, D.V., Org. Chem., 1988, vol. 53, no. 16, pp. 3758–3761.
Pedras, M.S.C., Chumala, P.B., Jin, W., Islam, M.S., and Hauck, D.W., Phytochemistry, 2009, vol. 70, no. 3, pp. 394–402.
Pedras, M.S. and Park, M.R., Mycologia, 2015, vol. 107, no. 6, pp. 1138–1150.
Meena, M., Swapnil, P., and Upadhyay, R.S., Sci. Rep., vol. 7, no. 1, p. 8777.
Wenderoth, M., Garganese, F., Schmidt-Heydt, M., Tobias, S.S., Ippolito, A., Sanzani, S.M., and Fischer, R., Mol. Microbiol., 2019, vol. 112, no. 1, pp. 131–146.
Yun, C.-S., Motoyama, T., and Osada, H., Nat. Commun., 2015, vol. 6, no. 1, p. 8758.
Avrova, A.O., Tyuterev, S.L., Evstigneeva, T.A., and Kozyreva, O.G., Mikol. Fitopatol., 1993, vol. 27, no. 6, pp. 52–56.
Svavov, S., Biotechnol. Biotechnol. Equip., 2009, vol. 23, no. SE, pp. 881–884. https://doi.org/10.1080/13102818.2009.10818563
Tan, K-C., Phan, H.T.T., Rybak, K., John, E., Chooi, Y.H., Solomon, P.S., and Oliver, R.P., Front. Plant Sci., 2015, vol. 6, no. 501, pp. 1–9.
RF Patent no. 2066347, 1996.
Courtial, J., Hamama, L., Helesbeux, J.-J., Lecomte, M., Renaux, Y., Guichard, E., Voisine, L., Yovanopoulos, C., Hamon, B., Ogé, L., Richomme, P., Briard, M., Boureau, T., Gagné, S., Poupard, P., and Berruyer, R., Front. Plant Sci., 2018, vol. 9, p. 502. https://doi.org/10.3389/fpls.2018.00502
Lal, R. and Lai, S., Crop Improvement Utilizing Biotechnology, Lal, R. and Lai, S., Eds., Boca Raton, FL: CRC Press, 2018.
Berestetskii, A.O., Vestnik Zashchity rastenii, 2017, vol. 91, no. 1, pp. 5–12.
Watson, A.K., in Weed Control: Sustainability, Hazards, and Risks in Cropping Systems Worldwide, Korres, N.E., Burgos, N.R., Duke, S.O., Eds., Boca Raton, FL: CRC Press, 2019.
Berestetskiy, A. and Sokornova, S., Biological Approaches for Controlling Weeds, Radhakrishnan, R., Ed., London: IntechOpen, 2018.
Andersen, G.L. and Lindow, S.E., Biological control of Carduus pycnocephalus with Alternaria sp., in Proc. VI Int. Symp. Biol. Contr. Weeds, Vancouver, Canada: E.S., Ed., Agric. Can., 1985, pp. 593–600.
Lawrie, J., Down, V.M., and Greaves, M.P., Biocontrol. Sci. Techn., 2000, vol. 10, no. 1, pp. 81–87.
Singh, J., Majumdar, D., Pandey, A., and Pandey, A.K., Recent Res. Sci. Technol., 2010, vol. 2, no. 9, pp. 22–27.
Motlagh, M.R.S., Afr. J. Microbiol. Res., 2012, vol. 6, no. 21, pp. 4481–4488.
Aneja, K.R., Kumar, P., and Sharma, C., J. Innov. Biol., 2014, vol. 1, no. 2, pp. 117–121.
Mabbayad M.O. and Watson A.K., J. Crop Prot., 1995, vol. 14, no. 5, pp. 429–433.
Green, S., Bailey, K.L., and Tewari, J.P., Mycol. Res., 2001, vol. 105, no. 3, pp. 344–351.
Gannibal, F.B. and Berestetskii, A.O., Mikol. Fitopatol., 2008, vol. 42, no. 2, pp. 110–118.
Cook, J.C., Charudattan, R., Zimmerman, T.W., Rosskopf, E.N., Stall, W.M., and Macdonald, G.E., Weed Technol., 2009, vol. 23, no. 4, pp. 550–555.
Vieira, B.S. and Barreto, R.W., Australas. Plant Pathol., 2010, vol. 39, no. 2, pp. 154–160.
Walker, H.L. and Sciumbato, G.L., Weed Res., 1979, vol. 27, no. 6, pp. 612–614.
RF Patent no. 2701957, 2019.
US Patent no 4636386, 1984.
US Patent no. 4755207, 1986.
US Patent no. 4776873, 1988.
US Patent no. 4915726, 1990.
Robeson, D., Strobel, G., Matusumoto, G.K., Fisher, E.L., Chen, M.H., and Clardy, J., Experientia, 1984, vol. 40, no. 11, pp. 1248–1250.
PRC Patent no. 101508959 A, 2008.
Sanodiya, B.S., Thakur, G.S., Baghel, R.K., Pandey, A.K., Prasad, G.B.K.S., and Bisen, P.S., J. Plant Prot. Res., 2010, vol. 50, no. 2, pp. 133–139.
Berestetskii, A.O., Yuzikhin, O.S., Katkova, A.S., Dobrodumov, A.V., Sivogrivov, D.E., and Kolombet, L.V., Appl. Biochem. Microbiol., 2010, vol. 46, no. 1, pp. 75–79.
Sassa, T., Horiguchi, K., and Suzuki, Y., Agric. Biol. Chem., 1989, vol. 53, no. 5, pp. 1337–1341.
Masi, M., Meyer, S., Clement, S., Pescitelli, G., Cimmino, A., Cristofaro, M., and Evidente, A., J. Nat. Prod., 2017, vol. 80, no. 10, pp. 2771–2777.
Varejão, E.V.V., Demuner, A.J., Barbosa, L.C., and Barreto, R.W., Quim. Nova, 2013, vol. 36, no. 7, pp. 1004–1007.
Haggblom, P., Microbiology, 1987, vol. 133, no. 12, pp. 3527–3529.
Kustrzeba-Wójcicka, I., Siwak, E., Terlecki, G., Wolańczyk-Mędrala, A., and Mędrala, W., Clin. Rev. Allergy Immunol., 2014, vol. 47, no. 3, pp. 354–365.
Hoagland, R.E., Boyette, C.D., Weaver, M.A., and Abbas, H.K., Toxin Rev., 2007, vol. 26, no. 4, pp. 313–342.
Pickett, J.A., Resistance'91: Achievements and Developments in Combating Pesticide Resistance, Dordrecht: Springer, 1992, pp. 354–365.
Shcherbakova, L.A., Natural Products in Plant Pest Management, Dubey, N.K., Ed., Wallingford: CABI International, 2011, pp. 109–133.
Lorsbach, B.A., Sparks, T.C., Cicchillo, R.M., Garizi, N.V., Hahn, D.R., and Meyer, K.G., Pest Manag. Sci., 2019, vol. 75, pp. 2301–2309.
La Croix, E.A.S., Mhasalkar, S.E., Mamalis, P., and Harrington, F.P., Pesti. Sci., 1975, vol. 6, no. 5, pp. 491–496.
Yang, F., Yang, B., Li, B., and Xiao, C., J. Zhejiang Univ. Sci., 2015, vol. 16, no. 4, pp. 264–274.
Singh, B., Bhagat, J., Chadha, B., and Kaur, A., Biologia, 2014, vol. 69, no. 1, pp. 10–14.
Bhagat, J., Kaur, A., Kaur, R., Yadav, A.K., Sharma, V., and Chadha, B.S., J. Appl. Microbiol., 2016, vol. 121, no. 4, pp. 1015–1025.
Male, K.B., Tzeng, Y.-M., Montes, J., Liu, B.-L., Lia-o, W.-C., Kamen, A., and Luong, J.H.T., Analyst, 2009, vol. 134, no. 7, pp. 1447–1452.
Musetti, R., Polizzotto, R., Vecchione, A., Borselli, S., Zulini, L., D’Ambrosio, Sanita` di Toppi, L., and Pertot, I., Micron, 2007, vol. 38, no. 6, pp. 643–650.
US Patent no. 20090257984 A1, 2009.
Solfrizzo, M., Vitti, C., De Girolamo, A., Visconti, A., Logrieco, A., and Fanizzi, F.P., J. Ag. Food Chem., 2004, vol. 52, no. 11, pp. 3655–3660.
Tal, B., Robeson, J.D., Burke, A.B., and Aasen, J.A., Phytochemistry, 1985, vol. 24, no. 4, pp. 729–731.
Robeson, D.J., Gray, G.R., and Strobel, G.A., Phytochemistry, 1982, vol. 21, no. 9, pp. 2359–2362.
Masi, M., Meyer, S., Clement, S., Cimmino, A., and Evidente, A., Nat. Prod. Res., 2019, vol. 5, pp. 1–9.
Aldrich, T.J., Rolshausen, P.E., Roper, M.C., Reader, J.M., Steinhaus, M.J., Rapicavoli, J., and Maloney, K.N., Phytochemistry, 2015, vol. 116, pp. 130–137.
Harding, D.P. and Raizada, M.N., Front. Plant Sci., 2015, vol. 6, p. 659. https://doi.org/10.3389/fpls.2015.00659
Heap, I., Pest Manage. Sci., 2014, vol. 70, no. 9, pp. 1306–1315.
Vaquera, S., Patriarca, A.G., and Cabrera, V.F., Eur. J. Plant Pathol., 2017, vol. 148, no. 4, pp. 1003–1009.
US Patent no. 5256628, 1993.
Abbas, H.K., Vesonderr, F., Boyette, C.D., and Peterson, S.W., Can. J. Bot., 1993, vol. 71, no. 1, pp. 155–160.
Abbas, H.K., Egley, G.H., and Paul, R.N., Phytopathology, 1995, vol. 85, no. 6, pp. 677–682.
Abbas, H., Phytochemistry, 1995, vol. 40, no. 6, pp. 1681–1689.
Chen, J., Mirocha, C.J., Xie, W., Hogge, L., and Olson, D., Appl. Environ. Microbiol., 1992, vol. 58, no. 12, pp. 3928–3931.
De Bruyne, L., Van Poucke, C., Di Mavungu, D.J., Zainudin, N.A.I.M., Vanhaecke, L., De Vleesschauwer, D., and Hofte, M., Mol. Plant Pathol., 2015, vol. 17, no. 6, pp. 805–817.
Lax, A.R., Shepherd, H.S., and Edwards, J.V., Weed Technol., 1988, vol. 2, no. 4, pp. 540–544.
Cavelier, F., Verducci, J., Andre, F., Haraux, F., Sigalat, C., Traris, M., and Vey, A., Pestic. Sci., 1998, vol. 52, no. 1, pp. 81–89.
Loiseau, N., Cavelier, F., Noel, J.-P., and Gomis, J.-M., J. Pept. Sci., 2002, vol. 8, no. 7, pp. 335–346.
Li, Y.-H., Han, W.-J., Gui, X.-W., Wei, T., Tang, S.-Y., and Jin, J.-M., Toxins, 2016, vol. 8, no. 8, p. 234. https://doi.org/10.3390/toxins8080234
WIPO Patent no. 159795A1, 2017.
Stierle, A.S., Cardellina, J.H., and Strobel, G.A., Proc. Natl. Acad. Sci. U. S. A., 1988, vol. 85, no. 21, pp. 8008–8011.
Bobylev, M.M., Bobyleva, L.I., and Strobel, G.A., J. Agric. Food Chem., 1996, vol. 44, no. 12, pp. 3960–3964.
US Patent no. 4929270, 1990.
Marsico, G., Ciccone, M.S., Masi, M., Freda, F., Cristofaro, M., Evidente, A., and Scafato, P., Molecules, 2019, vol. 24, no. 17, p. 3193. https://doi.org/10.3390/molecules24173193
Solfrizzo, M., Girolamo, A.D., Vitti, C., Tylkowska, K., Grabarkiewicz-Szczesna, J., Szopińska, D., and Dorna, H., Food Addit. Contam. Part A Chem. Anal. Control Expo. Risk Assess., 2005, vol. 22, no. 4, pp. 302–308.
EU Patent no. 1849361 A1, 2005.
Chen, S. and Qiang, S., Pestic. Biochem. Phys., 2017, vol. 143, pp. 252–257.
Qiang, S. and Zhou, B., Am. Eurasian J. Environ. Agric. Sci., 2007, vol. 26, pp. 572–576.
Zhou, B., Wang, H., Meng, B., Wei, R., Wang, L., An, C., Chen, S., Yang, C., and Qiang, S., Pest Manage. Sci., 2019, vol. 75, pp. 2482–2489.
Sharma, S., Hameed, S., and Fatima, Z., Recent Pat. Biotechnol., 2016, vol. 10, no. 2, pp. 167–174.
Dinic, J., Podolski-Renic, A., Stankovic, T., Bankovic, J., and Pesic, M., Curr. Pharm. Des., 2015, vol. 21, no. 38, pp. 5589–5604.
Huang, C., Jin, H., Song, B., Zhu, X., Zhao, H., Cai, J., and Lin, Y., Appl. Microbiol. Boitechnol., 2011, vol. 93, no. 2, pp. 777-785.
Teiten, M.H., Mack, F., Debbab, A., Aly, A.H., Dicato, M., Proksch, P., and Diederich, M., Bioorg. Med. Chem., 2013, vol. 21, no. 13, pp. 3850–3858.
Liu, B.-L. and Tzeng, Y.-M., Biotechnol. Adv., 2012, vol. 30, no. 6, pp. 1242–1254.
Yeh, C.-T., Rao, Y.K., Ye, M., Wu, W.-S., Chang, T.-C., Wang, L.-S., and Tzeng, Y.-M., Toxicol. Appl. Pharm., 2012, vol. 261, no. 1, pp. 31–41.
Huynh, T.-T., Rao, Y.K., Lee, W.-H., Chen, H.-A., Le, T.D.-Q., Tzeng, D.T.W., and Yeh, C.-T., Toxicol. In Vitro, 2014, vol. 28, no. 4, pp. 552–561.
Chao, P.-Z., Chin, Y.-P., Hsu, I.-U., Liu, C.-M., Yu, Y.-C., Leung, T.-K., and Lin, Y.-F., Toxicol. In Vitro, 2013, vol. 27, no. 6, pp. 1870–1876.
Heilos, D., Rohrl, C., Pirker, C., Englinger, B., Baie-r, D., Mohr, T., et al., Oncotarget, 2018, vol. 9, no. 39, pp. 25661–25680.
Kwon, H.J., Owa, T., and Hassig, C.A., Proc. Natl. Acad. Sci. U. S. A., 1998, vol. 95, no. 7, pp. 3356–3361.
Togashi, K., Kakeya, H., Morishita, M., Song, Y.X., and Osada, H., Oncol. Res., 1998, vol. 10, no. 9, pp. 449–453.
Pang, X., Lin, X., Wang, P., Zhou, X., Yang, B., Wang, J., and Liu, Y., Mar. Drugs, 2018, vol. 16, no. 8, p. 280. https://doi.org/10.3390/md16080280
Johann, S., Rosa, L.H., Rosa, C.A., Perez, P., Cisalpino, P.S., Zani, C.L., and Cota, B.B., Rev. Iberoam. Micol., 2012, vol. 29, no. 4, pp. 205–209.
Cimmino, A., Pescitelli, G., Berestetskiy, A., Dalinova, A., Krivorotov, D., Tuzi, A., and Evidente, A., J. Antibiot., 2015, vol. 69, no. 1, pp. 9–14.
Kwon, H.J., Kim, J.-H., Kim, M., Lee, J.-K., Hwang, W.-S., and Kim, D.-Y., Vet. Parasitol., 2003, vol. 112, no. 4, pp. 269–276.
Cota, B.B., Rosa, L.H., Caligiorne, R.B., Rabello, A.L.T., Alves, T.M.A., Rosa, C.A., and Zani, C.L., FEMS Microbiol. Lett., 2008, vol. 285, no. 2, pp. 177–182.
Bashyal, B.P., Wellensiek, B.P., Ramakrishnan, R., Faeth, S.H., Ahmad, N., and Gunatilaka, A.A.L., Bioorg. Med. Chem., 2014, vol. 22, no. 21, pp. 6112–6116.
Zheng, C.-J., Shao, C.-L., Guo, Z.-Y., Chen, J.-F., Deng, D.-S., Yang, K.-L., and Wang, C.-Y., J. Nat. Prod., 2012, vol. 75, no. 2, pp. 189–197.
Chua, S.W., Cornejo, A., van Eersel, J., Stevens, C.H., Vaca, I., Cueto, M., and Ittner, L.M., ACS Chem. Neurosci., 2017, vol. 8, no. 4, pp. 743–751.
Zheng, Z., Zhao, Z., Li, S., Lu, X., Jiang, M., Lin, J., and Xie, W., Mol. Pharm., 2017, vol. 92, no. 4, pp. 425–436.
PRC Patent no. 103054843B, 2012.
Garcнa -Ruiz, C., Cheng-Sánchez, I., and Sarabia, F., Org. Lett., 2015, vol. 17, no. 22, pp. 5558–5561.
Podlech, J. and Cudaj, J., Synlett, 2012, vol. 23, no. 3, pp. 371–374.
Frisvad, J.C., Front. Microbiol., 2015, vol. 5, p. 773. https://doi.org/10.3389/fmicb.2014.00773
Andersen, B., Sorensen, J.L., Nielsen, K.F., Ende, B.G., and de Hoog, S., Fungal Genet. Biol., 2009, vol. 46, no. 9, pp. 642–656.
Andersen, B., Hansen, M.E., and Smedsgaard, J., Phytopathology, 2005, vol. 95, no. 9, pp. 1021–1029.
Lakshmi, M.J., Chowdappa, P., and Mahmood, R., Indian Phytopathol., vol. 67, no. 4, pp. 374–382.
Patriarca, A., Cruz, CabralL., Pavicich, M.A., Nielsen, K.F., and Andersen, B., Int. J. Food Microbiol., 2019, vol. 291, pp. 135–143.
Andersen, B. and Thrane, U., Mycotoxin Res., 1996, vol. 12, no. 2, pp. 54–60.
Zwickel, T., Kahl, S.M., Rychlik, M., and Muller, M.E.H., Front. Microbiol., 2018, vol. 9, pp. 1368.
Larsen, T.O., Perry, N.B., and Andersen, B., Tetrahedron Lett., 2003, vol. 44, no. 24, pp. 4511–4513.
Andersen, B., Kroger, E., and Roberts, R.G., Mycol. Res., 2002, vol. 106, no. 2, pp. 170–182.
Somma, S., Amatulli, M.T., Masiello, M., Moretti, A., and Logrieco, A.F., Int. J. Food Microbiol., 2019, vol. 293, pp. 34–43.
Andersen, B., Dongo, A., and Pryor, B.M., Mycol. Res., 2008, vol. 112, no. 2, pp. 241–250.
Brun, S., Madrid, H., Gerrits, VanDen., Ende, B., Andersen, B., Marinach-Patrice, C., Mazier, D., and De Hoog, G.S., Fungal Biol., 2013, vol. 117, no. 1, pp. 32–40.
Orina, A.S., Gannibal, F.B., Mironenko, N.V., and Levitin, M.M., Mykol. Fitopatol., 2014, vol. 48, no. 1, pp. 53–62.
Funding
The work was supported financially by the Russian Science Foundation (project no. 16-16-00085).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated by T. Borisova
Rights and permissions
About this article
Cite this article
Dalinova, A.A., Salimova, D.R. & Berestetskiy, A.O. Fungi of the Genera Alternaria as Producers of Biological Active Compounds and Mycoherbicides. Appl Biochem Microbiol 56, 256–272 (2020). https://doi.org/10.1134/S0003683820030023
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0003683820030023