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Genotoxic and mutagenic properties of synthetic betulinic acid and betulonic acid

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Abstract

Betulinic acid was synthesized from birch bark extract (Betula pendula), with betulonic acid being an intermediate of the synthesis. Both compounds were isolated with a purity of 95%. Genotoxicity and mutagenicity of the prepared compounds was analyzed by the Ames test and SOS chromotest and it was found that the substances show no mutagenic and genotoxic activity.

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Abbreviations

NQO:

4-nitroquinolin-1-oxide

MTBE:

methyl tert-butyl ether

t-BuO2H:

tert-butyl hydroperoxide

References

  1. Bishayee, A., Ahmed, S., Brankov, N., and Perloff, M., Front Biosci, 2011, vol. 16, pp. 980–996.

    Article  CAS  Google Scholar 

  2. Tolstikov, G.A., Flekhter, O.B., Shul’ts, E.E., Baltina, L.A, and Tolstikov, A.G., Khim. Interesah Ustoich. Razvit., 2005, no. 30, pp. 1–30.

    Google Scholar 

  3. Rzeski, W., Stepulak, A., Szymanski, M., Sifringer, M., Kaczor, J., Wejksza, K., Zdzisinska, B., and Kandefer-Szerszen, M., Naunyn Schmiedebergs Arch. Pharmacol., 2006, vol. 374, pp. 11–20.

    Article  CAS  PubMed  Google Scholar 

  4. Yogeeswari, P. and Sriram, D., Curr. Med. Chem., 2005, vol. 12, pp. 657–666.

    Article  CAS  PubMed  Google Scholar 

  5. Liu, E.H., Qi, L.W., Wu, Q., Peng, Y.B., and Li, P., Mini Rev. Med. Chem., 2009, vol. 9, pp. 1547–1555.

    Article  CAS  PubMed  Google Scholar 

  6. Damle, A.A., Pawar, Y.P., and Narkar, A.A., Indian J. Exp. Biol., 2013, vol. 51, pp. 458–491.

    Google Scholar 

  7. Micali, G., Lacarrubba, F., Bhatt, K., and Nasca, M.R., Expert Rev. Anticancer Ther., 2013, vol. 12, pp. 9–21.

    Google Scholar 

  8. Chintharlapalli, S., Papineni, S., Lei, P., Pathi, S., and Safe, S., BMC Cancer, 2011, vol. 11, p. 371.

  9. Chintharlapalli, S., Papineni, S., Ramaiah, S.K., and Safe, S., Cancer Res., 2007, vol. 67, pp. 2816–2823.

    Article  CAS  PubMed  Google Scholar 

  10. Bache, M., Zschornak, M.P., Passin, S., Kessler, J., Wichmann, H., Kappler, M., Paschke, R., Kaluđerović, G.N., Kommera, H., Taubert, H., and Vordermark, D., Radiat. Oncol., 2011, vol. 6, p. 111.

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  11. Fulda, S. and Debatin, K.M., Med. Pediatr. Oncol., 2000, vol. 6, pp. 616–618.

    Article  Google Scholar 

  12. Fulda, S. and Kroemer, G., Drug Discov. Today, 2009, vol. 14, pp. 17–18.

    Article  Google Scholar 

  13. Petronelli, A., Pannitteri, G., and Testa, U., Anticancer Drugs, 2009, vol. 10, pp. 880–892.

    Article  Google Scholar 

  14. Mullauer, F.B., Kessler, J.H., and Medema, J.P., Anticancer Drugs, 2010, vol. 21, pp. 215–227.

    Article  CAS  PubMed  Google Scholar 

  15. Reiner, T., Parrondo, R., Pozas, A., Palenzuela, D., and Perez-Stable, C., PLoS One, 2013, vol. 8, pp. 1–11.

    Article  Google Scholar 

  16. Szuster-Cieseilska, A. and Kandefer-Szerseń, M., Pharmacol. Rep., 2005, vol. 57, pp. 588–595.

    Google Scholar 

  17. Silva, M., David, J.P., Silva, L., Santos, R., David, J.M., Lima, L., and Fontana, R., Molecules, 2012, vol. 17, pp. 12197–12205.

    Article  PubMed  Google Scholar 

  18. Padilha, M.M., Vilela, F.C., Rocha, C.Q., Dias, M.J., Soncini, R., dos Santos, M.H., Alves-da-Silva, G., and Giusti-Paiva, A., Phytother. Res., 2010, vol. 24, pp. 1496–1500.

    Article  CAS  PubMed  Google Scholar 

  19. Kim, J., Lee, Y.S., Kim, C.S., and Kim, J.S., Phytother. Res., 2011, vol. 11, p. 3672.

  20. Presnova, G.A., Chistyakov, A.N., and Durnev, A., Bull. Exp. Biol. Med., 2004, vol. 138, pp. 475–478.

    Article  PubMed  Google Scholar 

  21. Melnikova, N., Burlova, I., Kiseleva, T., Klabukova, I., Gulenova, M., Kislitsin, A., Vasin, V., and Tanaseichuk, B., Molecules, 2012, vol. 17, pp. 11849–11863.

    Article  CAS  PubMed  Google Scholar 

  22. Tolstikova, T.G., Sorokina, I.V., Tolstikov, G.A., Tolstikov, A.G., and Flechter, O.B, Russ. J. Bioorg. Chem., 2006, vol. 32, pp. 261–276.

    Article  CAS  Google Scholar 

  23. Kislitsin, A.N., Wood Chem., 1994, vol. 3, pp. 3–28.

    Google Scholar 

  24. Aiken, C. and Chen, C.H., Trends Mol. Med., 2005, vol. 11, pp. 31–36.

    Article  CAS  PubMed  Google Scholar 

  25. Motteran, L., Pilone, M.S., Molla, G., Ghisla, S., and Pollegioni, L., J. Biol. Chem., 2001, vol. 276, pp. 18024–18030.

    Article  CAS  PubMed  Google Scholar 

  26. Bastos, D.Z.L., Pimentel, I.C., De Jesus, D.A., and De Oliveira, B.H., Phytochemistry, 2007, vol. 68, pp. 834–839.

    Article  CAS  PubMed  Google Scholar 

  27. Pavlova, N.I., Savinova, O.V., Nikolaeva, S.N., Boreko, E.I., and Flekhter, O.B., Fitoterapia, 2003, vol. 74, pp. 489–492.

    Article  CAS  PubMed  Google Scholar 

  28. Savinova, O.V., Pavlova, N.I., and Boreko, E.I., Antibiot. Khimioter., 2009, vol. 54, pp. 16–20.

    CAS  PubMed  Google Scholar 

  29. Bridges, B.A., Environ. Health Perspect., 1973, vol. 6, pp. 221–227.

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  30. Kogai, T.I., Zh. Sibirsk. Feder. Univ., 2008, no. 1, pp. 97–104.

    Google Scholar 

  31. Kweyu, P.L., Bii, C., Akenga, A.T., and Wanjala, W.C., Antimicrobial marine natural products from the sponge, Axinella infundibuliformis, Rec. Nat. Prod., 2008, vol. 2, pp. 116–127.

    Google Scholar 

  32. Lee, T.-H., Juang, S.H., Hsu, F.-L., and Wu, C.-Y., Triterpene acids from the leaves of Planchonella duclitan (Blanco) Bakhuizan, J. Chinese Chem. Soc., 2005, vol. 52, pp. 1275–1280.

    CAS  Google Scholar 

  33. Escandani, M., Hamishenkar, H., Ezzati, Nazhad., and Dolatabadi, J., Food Chem., 2014, vol. 153, pp. 315–320.

    Article  Google Scholar 

  34. Quillardet, P. and Hofnung, M., J. Bacteriol., 1984, vol. 157, pp. 35–38.

    CAS  PubMed Central  PubMed  Google Scholar 

  35. Quillardet, P., Huisman, O., D’Ari, R., and Hofnung, M., Proc. Natl. Acad. Sci. U.S.A., 1982, vol. 79, pp. 5971–5975.

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  36. Quillardet, P. and Hofnung, M., Mutat. Res., 1985, vol. 147, pp. 65–78.

    Article  CAS  PubMed  Google Scholar 

  37. Mersch-Sundermann, V., Kevekordes, S., and Mochayedi, S., Mutat. Res., 1991, vol. 51, no. 60, pp. 51–50.

    Article  Google Scholar 

  38. Ames, B.N., McCann, J., and Yamasaki, E., Mutat. Res., 1975, vol. 31, pp. 347–364.

    Article  CAS  PubMed  Google Scholar 

  39. Maron, D.M. and Ames, B.N., Mutat. Res., 1983, vol. 113, nos. 3–4, pp. 173–215.

    Article  CAS  PubMed  Google Scholar 

  40. Levin, D.E., Hollstein, M., Christman, M.F., Schwiers, E.A., and Ames, B.N., Proc. Natl. Acad. Sci. U.S.A., 1982, vol. 79, pp. 7445–7449.

    Article  CAS  PubMed Central  PubMed  Google Scholar 

  41. Levin, D.E., Hollstein, M., Christman, M.F., and Ames, B.N., Methods Enzymol., 1984, vol. 105, pp. 249–254.

    Article  CAS  PubMed  Google Scholar 

  42. Vasil’eva, L.A., Statisticheskie metody v biologii, meditsine i sel’skom khozyaistve (Statistical Methods in Biology, Medicine, Agriculture, and Farming), Novosibirsk: Inst. Tsitol. Genet. SO RAN, 2007.

    Google Scholar 

  43. Hudson, D., Statistika dlya fizikov (Statistics for Physicists), Moscow: Mir, 1970.

    Google Scholar 

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Author information

Authors and Affiliations

  1. Novosibirsk State University, Novosibirsk, 630090, Russia

    T. S. Frolova

  2. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Novosibirsk, Russia

    T. S. Frolova & T. P. Kukina

  3. Institute of Cytology and Genetics, Siberian Branch, Russian Academy of Sciences, Novosibirsk, Russia

    O. I. Sinitsyna

Authors
  1. T. S. Frolova
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  2. T. P. Kukina
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  3. O. I. Sinitsyna
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Correspondence to T. S. Frolova.

Additional information

Original Russian Text © T.S. Frolova, T.P. Kukina, O.I. Sinitsyna, 2015, published in Bioorganicheskaya Khimiya, 2015, Vol. 41, No. 4, pp. 462–467.

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Frolova, T.S., Kukina, T.P. & Sinitsyna, O.I. Genotoxic and mutagenic properties of synthetic betulinic acid and betulonic acid. Russ J Bioorg Chem 41, 409–413 (2015). https://doi.org/10.1134/S1068162015040056

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  • DOI: https://doi.org/10.1134/S1068162015040056

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