Examples



mdbootstrap.com



 
Статья
2021

Heptaene Macrolide Antibiotic Perimycin: Preparation, Physicochemical Properties, Structure, Biological Activity, and Application in Agriculture as an Eco-Friendly Fungicide (A Review)


V. V. BelakhovV. V. Belakhov
Российский журнал общей химии
https://doi.org/10.1134/S1070363221130235
Abstract / Full Text

Published data on the preparation, physicochemical properties, chemical structure, and biological activity of heptaene macrolide antibiotic perimycin were systematically described. Various directions of practical application of perimycin in agriculture as an eco-friendly antifungal preparation were summarized.

Author information
  • Schulich Faculty of Chemistry, Technion – Israel Institute of Technology, 3200008, Haifa, IsraelV. V. Belakhov
References
  1. Tereshin, I.M., Polyene Antibiotics – Present and Future, Tokyo: Univ.of Tokyo Press, 1976.
  2. Macrolide Antibiotics: Chemistry, Biology, and Practice, Omura, S., Ed., New York: Academic, 2002.
  3. Zotchev, S.B., Curr. Med. Chem., 2003, vol. 10, no. 3, p. 211. https://doi.org/10.2174/0929867033368448
  4. Sergeev, A.Yu. and Sergeev Yu.V., Gribkovye infektsii. Rukovodstvo dlya vrachei (Fungal Infections. A Guide for Physicians), Moscow: BINOM, 2008, p. 142.
  5. Kozlov, S.N. and Strachunskii, L.S., Sovremennaya antimikrobnaya khimioterapiya (Modern Antimicrobial Chemotherapy), Moscow: Meditsinskoe Informatsionnoe Agentstvo, 2009, p. 19.
  6. Reiss, E., Shadomy, H.J., and Lyon, G.M., Fundamental Medical Mycology, Hoboken (NJ, USA): Willey-Blackwell, 2011.
  7. Belakhov, V.V., Garabadzhiu, A.V., and Chistyakova, T.B., Pharm. Chem. J., 2019, vol. 52, no. 11, p. 890. https://doi.org/10.1007/s11094-019-01922-3
  8. Oswald, E.J., Reedy, R.J., and Randall, W.A., Antibiot. Ann., vols. 1955–1956, 1956, p. 236.
  9. Wooldridge, W.E., UK Patent 828792, Chem. Abstr., 1960, vol. 54, 82931.
  10. Wooldridge, W.E., US Patent 2956925, Chem. Abstr., 1961, vol. 55, 19732.
  11. McDaniel, L.E., Schaffner, C.P., and Bailey, E.G., US Patent 3182004, Chem. Abstr., 1965, vol. 63, 20124.
  12. Mohan, R.R., Pianotti, R.S., Martin, J.F., Ringel, S.M., Schwartz, B.S., Bailey, E.G., McDaniel, L.E., and Schaffner, C.P., Antimicrob. Agents Chemother., 1964, vol. 1963, p. 462.
  13. Borowski, E., Schaffner, C.P., Lechevalier, H., and Schwartz, B.S., Antimicrob. Annu., 1960, 1961, vol. 1960, p. 532.
  14. Lechevalier, H., Borowski, E., Lampen, J.O., and Schaffner, C.P., Antibiot. Chemother., 1961, vol. 11, p. 640.
  15. Campbell, C.C., Hill, G.B., and Brooks, B.E., Antibiot. Ann., 1956, vols. 1955–1956, p. 240.
  16. Lynch, H.J., Furcolow, M.L., Yates, J.L., Tosh, F.E., and Larsh, H.W., Antimicrob. Agents Annu., 1961, vol. 1960, p. 551.
  17. Kumar, K., Gupta, S.C., Chander Y., and Singh, A.K., in Advances in Agronomy, Sparks, D., Ed., Oxford (UK): Elsevier, 2005, vol. 87, p. 1.
  18. Basic and Applied Aspects of Biopesticides, Sahayaraj, K., Ed., New Delhi (India): Springer, 2014.
  19. Antibiotics: Current Innovations and Future Trends, Sanchez, S. and Demain, A.L. Eds., Norfolk (UK): Caister Academic, 2015, p. 113.
  20. Shternshis, M.V., Biologicheskaya zashchita rastenii (Biological Protection of Plants), Moscow: Kolos, 2004.
  21. Mel’nikov, N.N., Pestitsidy. Khimiya, tekhnologiya i primenenie (Pesticides: Chemistry, Technology, and Application), Moscow: Khimiya, 1987, p. 674.
  22. Egorov, N.S., Osnovy ucheniya ob antibiotikakh (Fundamentals of the Doctrine of Antibiotics), Moscow: Mosk. Gos. Univ., 6th ed., 2004, p. 492.
  23. Biopesticides: State of the Art and Future Opportunities, Gross, A., Coats, J.R., Duke, S.O., and Seiber, J.N., Eds., Washington: American Chemical Society, 2015.
  24. Copping, L.G. and Duke, S.O., Pest Manag. Sci., 2007, vol. 63, no. 6, p. 524. https://doi.org/10.1002/ps.1378
  25. Nollet, L.M.L. and Rathore, H.S., Biopesticides Handbook, Boca Raton (FL, USA): CRC Press Taylor & Francis Group, 2015.
  26. Watson, D., Pesticide Management and Insecticide Resistance, New York: Elsevier Science, 2012.
  27. Singh, D.K., Pesticide Chemistry and Toxicology, Danvers (MA, USA): Bentham Science, 2012, vol. 1.
  28. Belakhov, V.V., Russ. J. Gen. Chem., 2020, vol. 90, no. 13, p. 2632. https://doi.org/10.1134/S1070363220130174
  29. Belakhov, V.V., Russ. J. Gen. Chem., 2021, vol. 91, no. 13, p. 2858. https://doi.org/10.1134/S1070363221130156
  30. Sukapure, P.W., Rahalkar, P.W., and Gharpure Y.H., in Antimicrobials and Agriculture: Proc. 4 Int. Symp. on Antibiotics in Agriculture: Benefits and Malefits, Woodbine, M., Ed., London: Butterworths, 1984, p. 137.
  31. Dhuley, J.N., Shanbhag, V., Raman, P.H., Mujumdar, A.M., and Naik, S.R., Indian J. Exp. Biol., 1995, vol. 33, no. 11, p. 857.
  32. Aparicio, J.F., Caffrey, P., Gil, J.A., and Zotchev, S.B., Appl. Microbiol. Biotechnol., 2003, vol. 61, no. 3, p. 179. https://doi.org/10.1007/s00253-002-1183-5
  33. Treshchalin, I.D., Sletta, H., Borgos, S.E.F., Pereverzeva, E.R., Voeikova, T.A., Elligsen, T.E., and Zotchev, S.B., Antibiot. Khimioter., 2005, vol. 50, no. 7, p. 18.
  34. Trenin, A.S., Antibiot. Khimioter., 2015, vol. 60, nos. 7–8, p. 34.
  35. Hutchinson, E., Murphy, B., Dunne, T., Breen, C., Rawlings, B., and Caffrey, P., Chem. Biol., 2010, vol. 17, no. 2, p. 174. https://doi.org/10.1016/j.chembiol.2010.01.007
  36. Caffrey, P., De Poire, E., Sheehan, J., and Sweeney, P., Appl. Microbiol. Biotechnol., 2016, vol. 100, no. 9, p. 3893. https://doi.org/10.1007/s00253-016-7474-z
  37. Kolodziejczyk, P., Zielinski, J., Pawlak, J., Golik, J., Falkowski, L., and Borowski, E., Tetrahedron Lett., 1976, vol. 17, no. 40, p. 3603. https://doi.org/10.1016/S0040-4039(00)92971-X
  38. Mechlinski, W. and Schaffner, C.P., J. Chromatogr., 1974, vol. 99, p. 619. https://doi.org/10.1016/S0021-9673(00)90890-2
  39. Lee, C.-H. and Schaffner, C.P., Tetrahedron, 1969, vol. 25, no. 10, p. 2229. https://doi.org/10.1016/S0040-4020(01)82770-8
  40. Borowski, E., Falkowski, L., Zielinski, J., Kolodziejczyk, P., Golik, J., Cybulska, B., Ziminski, T., Jereszek, E., Pawlak, J., Shenin, Yu.D., and Tereshin, I.M., Khim.-Farm. Zh., 1977, vol. 11, no. 11, p. 57.
  41. Pawlak, J., Sowinski, P., and Borowski, E., J. Antibiot., 1995, vol. 48, no. 9, p. 1034. https://doi.org/10.7164/antibiotics.48.1034
  42. Lee, C.-H. and Schaffner, C.P., Tetrahedron Lett., 1966, vol. 7, no. 47, p. 5837. https://doi.org/10.1016/S0040-4039(00)76093-X
  43. El Khadem, H. and El Ashry, S.H., Carbohydr. Res., 1968, vol. 7, no. 4, p. 501. https://doi.org/10.1016/S0008-6215(00)82974-2
  44. Stevens, C.L., Gupta, S.K., Glinski, R.P., Taylor, K.G., Blumbergs, P., Schaffner, C.P., and Lee, C.-H., Carbohydr. Res., 1968, vol. 7, no. 4, p. 502. https://doi.org/10.1016/S0008-6215(00)82975-4
  45. Stevens, C.L., Glinski, R.P., Taylor, K.G., Blumbergs, P., and Gupta, S.K., J. Am. Chem. Soc., 1970, vol. 92, no. 10, p. 3160. https://doi.org/10.1021/ja00713a039
  46. Pansy, F., Jambor, W.P., Wilber-Murphy, J., and Gadebusch, H.H., J. Antibiot., 1972, vol. 25, no. 78, p. 405. https://doi.org/10.7164/antibiotics.25.405
  47. Vetlugina, L.A. and Nikitina, E.T., Protivogribkovye polienovye antibiotiki (Antifungal Polyene Antibiotics), Alma-Ata: Nauka, 1980, p. 7.
  48. Shenin, Yu. D., Belakhov, V.V., and Araviisky, R.A., Pharm. Chem. J., 1993, vol. 27, no. 2, p. 84.
  49. Shenin, Yu.D. and Belakhov, V.V., Antibiot. Khimioter., 1997, vol. 42, no. 4, p. 34.
  50. Gale, E.F., J. Gen. Microbiol., 1974, vol. 80, part 2, p. 451. https://doi.org/10.1099/00221287-80-2-451
  51. Cybulska, B., Mazerski, J., Zielinski, J., Ziminski, T., and Borowski, E., Drugs Exp. Clin. Res., 1980, vol. 6, no. 5, p. 449.
  52. Cybulska, B., Mazerski, J., Borowski, E., and GaryBobo, C.M., Biochem. Pharmacol., 1984, vol. 33, no. 1, p. 41. https://doi.org/10.1016/0006-2952(84)90368-X
  53. Mikolajczyk, E., Photochem. Photobiol., 1986, vol. 43, no. 4, p. 455. https://doi.org/10.1111/j.1751-1097.1986.tb05629.x
  54. Cybulska, B., Herve, M., Borowski, E., and GaryBobo, C.M., Mol. Pharmacol., 1986, vol. 29, no. 3, p. 293.
  55. Herve, M., Debouzy, J.C., Borowski, E., Cybulska, B., and Gary-Bobo, C.M., Biochim. Biophys. Acta, 1989, vol. 980, no. 3, p. 261.
  56. Cybulska, B., Borowski, E., and Gary-Bobo, C.M., Biochem. Pharmacol., 1989, vol. 38, no. 11, p. 1755. https://doi.org/10.1016/0006-2952(89)90409-7
  57. Gary-Bobo, C.M., Biochimie, 1989, vol. 71, no. 1, p. 37. https://doi.org/10.1016/0300-9084(89)90129-6
  58. Michalska, E., Chemotherapia, 1964, vol. 9, no. 1, p. 52.
  59. Michalska-Trenkner, E., Chemotherapia, 1970, vol. 15, no. 1, p. 19.
  60. Schaffner, C.P. and Borowski, E., US Patent 3244590, Chem. Abstr., 1966, vol. 64, 104639.
  61. Hrabowska, M., Acta Biol. Med., 1969, vol. 14, no. 3, p. 227.
  62. Schaffner, C.P. and Borowski, E., Antibiot. Chemother., 1961, vol. 11, p. 724.
  63. Mazerski, J., Bolard, J., and Borowski, E., Biochim. Biophys. Acta, 1982, vol. 719, no. 1, p. 11. https://doi.org/10.1016/0304-4165(82)90300-2
  64. Falkowski, L., Stefanska, B., Zielinski, J., Bylec, E., Golik, J., and Kolodziejczyk, P., Acta Polon. Pharm., 1980, vol. 37, no. 6, p. 631.
  65. Falkowski, L., Stefanska, B., Zielinski, J., Troka, E., Golik, J., Kolodziejczyk, P., Jarzebski, А., Cybulska, B., and Borowski, E., USSR Inventor’s Certificate no. 955855, Byull. Izobert., 1982, no. 32.
  66. Czerwinski, A., Grzybowska, J., and Borowski, E., J. Antibiot., 1986, vol. 39, no. 7, p. 1025. https://doi.org/10.7164/antibiotics.39.1025
  67. Baldwin, C., Chang, C.C., and Dang, B.T., US Patent 6562796, Chem. Abstr., 2001, vol. 135, 92803.
  68. Ogawa, T. and Yamamoto, A., US Patent 10028903, Chem. Abstr., 2010, vol. 152, 415391.
  69. Tyuterev, S.L., Obrabotka semyan fungitsidami i drugimi sredstvami optimizatsii zhizni rastenii (Seed Treatment with Fungicides and Other Means of Optimizing Plant Life), St. Petersburg: Vseross. Nauchno-Issled. Inst. Zashchity Rastenii, 2006.
  70. Shternshis, M.V., Vestn. Tomsk. Gos. Univ., Biologiya, 2012, no. 2, p. 92.
  71. Gol’din, E.B., Geopolit. Ekogeodin. Reg., 2014, vol. 10, no. 2, p. 99.
  72. Zakharenko, V.A., Agrokhimiya, 2015, no. 6, p. 64.
  73. Zhemchuzhin, S.G., Spiridonov, Yu.Ya., and Bosak, G.S., Agrokhimiya, 2019, no. 11, p. 77.
  74. Kumar, V., Int. J. Agricul. Sci. Res., 2015, vol. 4, no. 8, p. 168.
  75. Yadav, A., Keval, R., and Choudhary, S., J. Agroecol. Nat. Resour. Manag., 2015, vol. 2, no. 1, p. 57. http://www.krishisanskriti.org/janrm.html
  76. Walia, S., Saha, S., Tripathi, V., and Sharma, K.K., Phytochem. Rev., 2017, vol. 16, no. 5, p. 989. https://doi.org/10.1007/s11101-017-9512-6
  77. Volova, T.G., Vvedenie v biotekhnologiyu (Introduction to Biotechnology), Krasnoyarsk: Sib. Fed. Univ., 2008, p. 162.
  78. The Pesticide Manual, Turner, J.A., Ed., 18th ed., Hampshire (UK): BCPC (British Crop Production Council), 2018.
  79. Tyuterev, S.L., Mekhanizmy deistviya fungitsidov na fitopatogennye griby (Mechanisms of Action of Fungicides on Phytopathogenic Fungi), Moscow: Niva, 2010.
  80. D’yakov, Yu.T. and Levitin, M.M., Invazii fitopatogennykh gribov (Invasions of Phytopathogenic Fungi), Moscow: Lenand, 2018.
  81. Gagkaeva, T.Yu., Gavrilova, O.P., Levitin, M.M., and Novozhilov, K.V., Prilozh. Zh. Zashch. Karant. Rast., 2011, no. 5.
  82. Shkalikov, V.A., Beloshapkina, O.O., Bukreev, D.D., Gorbachev, I.V., Dzhalilov, F.S.-U., Korsak, I.V., Minaev, V.Yu., and Stroikov, Yu.M., Zashchita rastenii ot boleznei (Plant Protection against Diseases), Moscow: KolosS, 2010.
  83. D’yakov, Yu.T., in Materialy VII Vserossiiskoi mikologicheskoi konferentsii “Bioticheskie svyazi gribov: mosty mezhdu tsarstvami” (Proc. VII All-Russian Mycological Conf. “Biotic Connections of Fungi: Bridges between Kingdoms”), Moscow: Mosk. Gos. Univ., 2015, p. 39.
  84. Levitin, M.M., Afanasenko, O.S., Gagkaeva, T.Yu., Gannibal, F.B., Gul’tyaeva, E.I., and Mironenko, N.V., Vestn. Zashch. Rast., 2019, no. 4(102), p. 5. https://doi.org/10.31993/2308-6459-2019-4-102-5-16
  85. Thomma, B.P.H.J., Mol. Plant Pathol., 2003, vol. 4, no. 4, p. 225. https://doi.org/10.1046/j.1364-3703.2003.00173.x
  86. Michielse, C.B. and Rep, M., Mol. Plant Pathol., 2009, vol. 10, no. 3, p. 311. https://doi.org/10.1111/j.1364-3703.2009.00538.x
  87. Aoki, T., O’Donnell, and Geiser, D.M., J. Gen. Plant Pathol., 2014, vol. 80, no. 3, p. 189. https://doi.org/10.1007/s10327-014-0509-3
  88. Munkvold, G.P., in Mycotoxigenic Fungi: Methods and Protocols, Moretti, A. and Susca, A., Eds., New York: Springer, 2017, vol. 1542, chap. 4, p. 51. https://doi.org/10.1007/978-1-4939-6707-0_4
  89. Tralamazza, S.M., Piacentini, K.C., Iwase, C.H.T., and de Oliveira Rocha, L., Curr. Opin. Food Sci., 2018, vol. 23, p. 57. https://doi.org/10.1016/j.cofs.2018.05.002
  90. Lee, H.B., Patriarca, A., and Magan, N., Microbiology, 2015, vol. 43, no. 2, p. 93. https://doi.org/10.5941/MYCO.2015.43.2.93
  91. Belan, S.R., Agrokhimiya, 2003, no. 11, p. 27.
  92. Gannibal, F.B., Zashch. Karant. Rast., 2017, no. 10, p. 6.
  93. Sokolova, G.D. and Glinushkin, A.P., Mikol. Fitopatol., 2020, vol. 54, no. 6, p. 391.
  94. Mittelman, M.W. and Alberte, R.S., PCT International Application (PCT/US2007/60897147), WO 2008/092006 A2, published July 31, 2008, Chem. Abstr., 2008, vol. 149, 208017.
  95. Griffin, J.H. and Judice, J.K., PCT International Application (PCT/US2003/0060663), WO 1999/64040 A1, published December 16, 1999, Chem. Abstr., 1999, vol. 132, 30817.
  96. Qin, X. and Xie, L., Chinese Patent Application CN 102495038 A, Chem. Abstr., 2012, vol. 157, 93600.
  97. Chen, Z., Zhou, Y., Wang, R., and Wang, L., Chinese Patent Application CN 102614829 A, Chem. Abstr., 2012, vol. 157, 298698.
  98. Su, H., Ma, Z., Ma, Y., Qin, L., and Tan, T., Chinese Patent Application CN 105153474 A, Chem. Abstr., 2015, vol. 164, 163782.
  99. Birnbaum, J.E., Blake, T., Ghannoum, M., Vallespir, S., Antonacci, R., and Ryan, M.P., PCT International Application (PCT/US2007/0092547), WO 2006/38490 A1, published April 26, 2007, Chem. Abstr., 2008, vol. 149, 339946.
  100. Birnbaum, J.E., Blake, T., Ghannoum, M., and Vallespir, S., PCT International Application (PCT/US2008/0220103), WO 2006/38490 A1, published September 11, 2008, Chem. Abstr., 2008, vol. 150, 17257.
  101. Page, S. and Garg, S., RF Patent 2666605, Byull. Izobret., 2018, no. 26.
  102. Brennan, A.B., Long, C.J., Bagan, J.W., Schumacher, J.F., and Spiecker, M.M., US Patent 9016221, Chem. Abstr., 2010, vol. 153, 440825.
  103. Onsoyen, E., Dessen, A., Thomas, D.W., Hill, K.E., Sletta, H., Tondervik, A., Klinkenberg, G., and Myrvold, R., European Patent Application EP2755481A1, Chem. Abstr., 2013, vol. 158, 427872.
  104. Onsoyen, E., Dessen, A., Thomas, D.W., Hill, K.E., Sletta, H., Tondervik, A., Klinkenberg, G., and Myrvold, R., PCT International Application (PCT/US2015/0126467), WO 2013/038197 A1, published May 7, 2015, Chem. Abstr., 2015, vol. 167, 285297.
  105. Popova, L.M., Kurzin, A.V., and Evdokimov, A.N., Pestitsidy (Pesticides), St. Petersburg: Prospekt Nauki, 2014, p. 110.
  106. Biopesticides and Bioagents: Novel Tools for Pest Management, Anwer, A., Ed., Boca Raton (FL, USA): CRC Press, 2017.
  107. Shternshis, M.V., Andreeva, I.V., and Tomilova, O.G., Biologicheskaya zashchita rastenii (Biological Protection of Plants), St. Petersburg: Lan’, 2018, p. 271.
  108. Zakharychev, V.V., Griby i fungitsidy (Mushrooms and Fungicides), 2nd ed., St. Petersburg: Lan’, 2019, p. 202.
  109. Biopesticides for Sustainable Agriculture, Birch, N. and Travis Glare, T., Eds., London: Burleigh Dodds Science Publishing, 2020.
  110. Biopesticides, Rakshit, A., Meena, V., Abhilash, P.C., Sarma, B.K., Singh, H.B., Fraceto, L., Parihar, M., and Kumar, A., Eds., vol. 2: Advances in Bio-inoculants, Cambridge (UK): Woodhead Publishing, 2021.