Advertisement

Chemistry of Natural Compounds

, Volume 44, Issue 6, pp 704–711 | Cite as

Synthesis of amino-acid derivatives of chrysin

  • M. V. VeselovskayaEmail author
  • M. M. Garazd
  • A. S. Ogorodniichuk
  • Ya. L. Garazd
  • V. P. Khilya
Article

Various conjugates of amino acids with chrysin in which the amino acid was bonded through the C- or N-terminus to the flavone were prepared using peptide chemistry methods (symmetric anhydrides and activated esters).

Key words

flavonoids flavones chrysin amino-acid derivatives 

Notes

Acknowledgment

We thank OAO Eksimed (Kiev, Ukraine) for help with performing the work.

References

  1. 1.
    J. B. Harborne and C. A. Williamson, Phytochemistry, 55, 481 (2000).PubMedCrossRefGoogle Scholar
  2. 2.
    B. H. Havsteen, Pharmacol. Ther., 96, 67 (2002).PubMedCrossRefGoogle Scholar
  3. 3.
    C. A. Williams, J. B. Harborne, M. Netman, J. Greenham, and J. Eagles, Phytochemistry, 46, 1349 (1997).PubMedCrossRefGoogle Scholar
  4. 4.
    V. M. Malikov and M. P. Yuldashev, Khim. Prir. Soedin., 299 (2002).Google Scholar
  5. 5.
    M. Cardenas, M. Marder, V. C. Blank, and L. P. Roguin, Bioorg. Med. Chem., 14, 2966 (2006).PubMedCrossRefGoogle Scholar
  6. 6.
    Y.-P. Lin, F.-L. Hsu, C.-S. Chen, J.-W. Chern, and M.-H. Lee, Phytochemistry, 68, 1189 (2007).PubMedCrossRefGoogle Scholar
  7. 7.
    G. Beyer and M. F. Melzig, Planta Med., 69, 1125 (2003).PubMedCrossRefGoogle Scholar
  8. 8.
    J. Vaya, S. Mahmood, A. Goldblum, M. Aviram, N. Volkova, A. Shaalan, R. Musa, and S. Tamir, Phytochemistry, 62, 89 (2003).PubMedCrossRefGoogle Scholar
  9. 9.
    K. Y. Park, S.-H. Lee, B.-K. Min, K.-S. Lee, J.-S. Choi, S. R. Chung, K. R. Min, and Y. Kim, Planta Med., 65, 457 (1999).PubMedCrossRefGoogle Scholar
  10. 10.
    T. Nagaoka, A. H. Banskota, Y. Tezuka, K. Midorikawa, K. Matsushige, and S. Kadota, Biol. Pharm. Bull., 26, 487 (2003).PubMedCrossRefGoogle Scholar
  11. 11.
    J. Duarte, R. Jimenez, I. C. Villar, F. Perez-Vizcaino, J. Jimenez, and J. Tamargo, Planta Med., 67, 567 (2001).PubMedCrossRefGoogle Scholar
  12. 12.
    I. C. Villar, R. Vera, M. Galisteo, F. O'Valle, M. Romero, A. Zarzuelo, and J. Duarte, Planta Med., 71, 829 (2005).PubMedCrossRefGoogle Scholar
  13. 13.
    H. Kuwabara, K. Mouri, H. Otsuka, R. Kasai, and K. Yamasaki, J. Nat. Prod., 66, 1273 (2003).PubMedCrossRefGoogle Scholar
  14. 14.
    N. Orsolic, I. Kosalec, and I. Basic, Biol. Pharm. Bull., 28, 694 (2005).PubMedCrossRefGoogle Scholar
  15. 15.
    K. S. Babu, T. H. Babu, P. V. Srinivas, K. H. Kishore, U. S. N. Murthy, and J. M. Rao, Bioorg. Med. Chem. Lett., 16, 221 (2006).CrossRefGoogle Scholar
  16. 16.
    E. Melliou and I. Chinou, Planta Med., 70, 515 (2004).PubMedCrossRefGoogle Scholar
  17. 17.
    M. del Rayo Camacho, J. D. Phillipson, S. L. Croft, V. Yardley, and P. N. Solis, Planta Med., 70, 70 (2004).CrossRefGoogle Scholar
  18. 18.
    S. S. Kang, J. Y. Lee, Y. K. Choi, G. S. Kim, and B. H. Han, Bioorg. Med. Chem. Lett., 14, 2261 (2004).PubMedCrossRefGoogle Scholar
  19. 19.
    I. C. Villar, R. Jimenez, M. Galisteo, M. F. Garcia-Saura, A. Zarzuelo, and J. Duarte, Planta Med., 68, 847 (2002).PubMedCrossRefGoogle Scholar
  20. 20.
    H. Mastuda, T. Morikawa, K. Ueda, H. Managi, and M. Yoshikawa, Bioorg. Med. Chem., 10, 3123 (2002).PubMedCrossRefGoogle Scholar
  21. 21.
    J.-S. Shin, K.-S. Kim, M.-B. Kim, J.-H. Jeong, and B.-K. Kim, Bioorg. Med. Chem. Lett., 9, 869 (1999).PubMedCrossRefGoogle Scholar
  22. 22.
    X. Zheng, W.-D. Meng, Y.-Y. Xu, J.-G. Cao, and F.-L. Qinga, Bioorg. Med. Chem. Lett., 13, 881 (2003).PubMedCrossRefGoogle Scholar
  23. 23.
    T. Zhang, X. Chen. L. Qu, J. Wu, R. Cuia, and Y. Zhao, Bioorg. Med. Chem., 12, 6097 (2004).Google Scholar
  24. 24.
    C.-L. Wang, H.-Q. Li, W.-D. Menga, and F.-L. Qinga, Bioorg. Med. Chem. Lett., 15, 4456 (2005).PubMedCrossRefGoogle Scholar
  25. 25.
    G. Comte, J.-B. Daskiewicz, C. Bayer, G. Conseil, A. Viornery-Vanier, C. Dumontet, A. Di Pietro, and D. Barron, J. Med. Chem., 44, 763 (2001).PubMedCrossRefGoogle Scholar
  26. 26.
    T. T. Dao, Y. S. Chi, J. Kim, H. P. Kim, S. Kim, and H. Park, Bioorg. Med. Chem. Lett., 14, 1165 (2004).PubMedCrossRefGoogle Scholar
  27. 27.
    H. Park, T. T. Dao, and H. P. Kim, Eur. J. Med. Chem., 40, 943 (2005).PubMedCrossRefGoogle Scholar
  28. 28.
    A. A. Gershkovich and V. K. Kibirev, Chemical Synthesis of Peptides [in Russian], Naukova Dumka, Kiev (1992), p. 71.Google Scholar
  29. 29.
    M. M. Garazd, V. V. Arkhipov, N. K. Proskurka, and V. P. Khilya, Khim. Geterotsikl. Soedin., 744 (1999).Google Scholar
  30. 30.
    M. M. Garazd, Ya. L. Garazd, and V. P. Khilya, Khim. Prir. Soedin., 29 (2001).Google Scholar
  31. 31.
    M. M. Garazd, Ya. L. Garazd, A. S. Ogorodniichuk, V. V. Shilin, A. V. Turov, and V. P. Khilya, Khim. Prir. Soedin., 466 (1998).Google Scholar
  32. 32.
    J. Kim, Y. Lee, H. Kim, S.-Y. Kang, K.-S. Park, J.-H. Cho, Y.-Y. Lee, B.-S. Kim, Y. Lim, and Y. Chong, Bull. Kor. Chem. Soc., 26, 2065 (2005).CrossRefGoogle Scholar
  33. 33.
    G. W. Anderson, J. Zimmerman, and F. M. Callahan, J. Am. Chem. Soc., 85, 3039 (1963).CrossRefGoogle Scholar
  34. 34.
    T. V. Shokol, A. S. Ogorodniichuk, V. V. Shilin, V. B. Milevskaya, and V. P. Khilya, Khim. Geterotsikl. Soedin., 482 (1998).Google Scholar
  35. 35.
    S. Saxena, J. K. Makrandi, and S. K. Grover, Synthesis, 697 (1985).Google Scholar
  36. 36.
    M. T. Briggs, G. L. S. Duncan, and C. W. Thornber, J. Chem. Res. Miniprint, 9, 2461 (1982).Google Scholar
  37. 37.
    Blaise, FRM 1406; Chem. Abstr., 58, 7911b (1963).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2008

Authors and Affiliations

  • M. V. Veselovskaya
    • 1
    Email author
  • M. M. Garazd
    • 1
  • A. S. Ogorodniichuk
    • 1
  • Ya. L. Garazd
    • 2
  • V. P. Khilya
    • 2
  1. 1.Institute of Bioorganic and Petroleum ChemistryNational Academy of Sciences of UkraineKievUkraine
  2. 2.Taras Shevchenko Kiev National UniversityKievUkraine

Personalised recommendations