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The antiviral activity of cyclopentane β,β′-triketones related to secondary metabolites of higher plants

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Abstract

The effect of 20 cyclopentane β,β′-triketones and their sodium salts on the development of infections caused by tobacco mosaic virus (TMV) in leaves of tobacco (Nicotiana tabacum L. cv. Xanthi-nc) has been studied. It has been shown that the strongest antiviral effect is produced by sodium salts of 2-acetyl-4,7-dithio-2,3,4,5,6,7-hexahydro-1H-inden-1,3-dione, 2-acetyl-4-oxa-7-thio-2,3,4,5,6,7-hexahydro-1H-inden-1,3-dione, and 2-acetyl-4,5-didodecylthiocyclopent-4-en-1,3-dione. These compounds at a concentration of 2 mg/mL decrease the number of local TMV-induced necroses formed on inoculated tobacco leaves by 98% and have no toxic effect on leaf tissues.

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Abbreviations

TMV:

tobacco mosaic virus

References

  1. Reunov, A.V., Virusnyi patogenez i zashchitnye mekhanizmy rastenii (Viral Pathogenesis and Defense Mechanisms of Plants), Vladivostok, 1999.

    Google Scholar 

  2. Chirkov, S.N., Appl. Biochem. Microbiol., 2002, vol. 38, no. 1, pp. 1–9.

    Article  CAS  Google Scholar 

  3. Davydova, V.N., Appl. Biochem. Microbiol., 2011, vol. 47, no. 1, pp. 103–108.

    Article  CAS  Google Scholar 

  4. Nagorskaya, V.P., Reunov, A.V., Lapshina, L.A., Davydova, V.N., and Ermak, I.M., Tsitologiya, 2011, vol. 53, no. 2, pp. 185–191.

    CAS  Google Scholar 

  5. Slováková, L., Lišková, M., Kákoniová, D., and Karácsonyi, Š., Eur. J. Plant Pathol., 2000, vol. 106, no. 6, pp. 543–553.

    Article  Google Scholar 

  6. Šubíkováková, I., and Farkaš, V., Z. Pflanzenkrankh. Pflanzensch, 1994, vol. 101, no. 1, pp. 128–131.

    Google Scholar 

  7. Reunov, A., Nagorskaya, V., Lapshina, L., Yermak, I., and Barabanova, A., J. Plant Diseases Protect., 2004, vol. 111, no. 1, pp. 165–172.

    CAS  Google Scholar 

  8. Barabanova, A.O., Ermak, I.M., Reunov, A.V., Nagorskaya, V.P., and Solov’eva, T.F., Rastit. Resur., 2006, vol. 42, no. 1, pp. 80–86.

    CAS  Google Scholar 

  9. Lapshina, L.A., Reunov, A.V., Nagorskaya, V.P., Zvyagintseva, T.N., and Shevchenko, N.M., Russ. J. Plant Physiol., 2006, vol. 53, no. 2, pp. 246–251.

    Article  CAS  Google Scholar 

  10. Reunov, A., Lapshina, L., Nagorskaya, V., Zvyagintseva, T., and Shevchenko, N., J. Plant Diseases Protect., 2009, vol. 116, no. 2, pp. 49–54.

    CAS  Google Scholar 

  11. Rozhnova, N.A., Odintsova, T.I., and Gerashchenkov, G.A., Russ. J. Plant Physiol., 2007, vol. 54, no. 6, pp. 776–781.

    Article  CAS  Google Scholar 

  12. Aldwinckle, H.S., Virology, 1975, vol. 66, no. 1, pp. 341–343.

    Article  CAS  PubMed  Google Scholar 

  13. Balazs, E. and Kiraly, Z., Phytopathol. Z., 1981, vol. 100, no. 2, pp. 356–360.

    Article  CAS  Google Scholar 

  14. Fraser, R.S.S. and Whenham, R.J., J. Gen. Virol., 1978, vol. 39, no. 1, pp. 191–194.

    Article  CAS  Google Scholar 

  15. Schuster, G., Phytopathol. Z., 1987, vol. 119, no. 3, pp. 262–271.

    Article  CAS  Google Scholar 

  16. Birch, A.J., J. Chem. Soc., 1951, no. 11, pp. 3026–3030.

    Google Scholar 

  17. Kiang, A.K., Lee, H.H., and Sim, K.Y., J. Chem. Soc., 1962, no. 11, pp. 4338–4345.

    Google Scholar 

  18. Lee, H.H., Tetrahedron Lett., 1968, no. 40, pp. 4243–4246.

    Google Scholar 

  19. Li, X.-C., Ferreira, O., Jacob, M.R., Zhang, R., Khan, S.I., ElSohly, H.N., Nagle, D.G., Smillie, T.J., Khan, I.A., Walker, L.A., and Clark, A.M., J. Am. Chem. Soc., 2004, vol. 126, no. 22, pp. 6872–6873.

    Article  CAS  PubMed  Google Scholar 

  20. Gilardoni, G., Clericuzio, M., Tosi, S., Zanoni, G., and Vidari, G., J. Nat. Prod., 2007, vol. 70, no. 1, pp. 137–139.

    Article  CAS  PubMed  Google Scholar 

  21. Lapshina, L.A., Shestak, O.P., Reunov, A.V., Novikov, V.L., and Anisimov, M.M., Rastit. Resur., 2006, vol. 42, pp. 107–113.

    CAS  Google Scholar 

  22. Shestak, O.P., Novikov, V.L., Martyyas, E.A., and Anisimov, M.M., Khim.-Farm. Zh., 2009, vol. 43, no. 9, pp. 16–19.

    Google Scholar 

  23. Shestak, O.P., Novikov, V.L., Martyyas, E.A., and Anisimov, M.M., Khim.-Farm. Zh., 2011, vol. 45, no. 8, pp. 8–11.

    Google Scholar 

  24. Forsen, S., Merenyi, F., and Nilsson, M., Acta Chem. Scand., 1964, vol. 18, no. 5, pp. 1208–1221.

    Article  CAS  Google Scholar 

  25. Shestak, O.P. and Novikov, V.L., Izv. Akad. Nauk, Ser. Khim., 2010, no. 1, pp. 82–91.

    Google Scholar 

  26. Shestak, O.P., Novikov, V.L., Prokof’eva, N.G., and Chaikina, E.L., Khim.-Farm. Zh., 1999, vol. 33, no. 12, pp. 5–8.

    Google Scholar 

  27. Otsuki, Y., Takebe, I., Onho, T., Fukuda, M., and Okada, Y., Proc. Natl. Acad. Sci. USA, 1977, vol. 74, no. 5, pp. 1913–1917.

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  28. Met’yuz, R., Virusy rastenii (Plant Viruses), Moscow, 1973.

    Google Scholar 

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Authors and Affiliations

  1. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch, Russian Academy of Sciences, pr. 100 Let Vladivostoku 159, Vladivostok, 690022, Russia

    L. A. Lapshina, O. P. Shestak, A. V. Reunov & V. L. Novikov

Authors
  1. L. A. Lapshina
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  2. O. P. Shestak
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  3. A. V. Reunov
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  4. V. L. Novikov
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Correspondence to L. A. Lapshina.

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Original Russian Text © L.A. Lapshina, O.P. Shestak, A.V. Reunov, V.L. Novikov, 2013, published in Khimiya Rastitel’nogo Syr’ya, 2013, No. 2, pp. 107–112.

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Lapshina, L.A., Shestak, O.P., Reunov, A.V. et al. The antiviral activity of cyclopentane β,β′-triketones related to secondary metabolites of higher plants. Russ J Bioorg Chem 40, 796–799 (2014). https://doi.org/10.1134/S1068162014070085

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  • DOI: https://doi.org/10.1134/S1068162014070085

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