Advertisement

Chemistry of Natural Compounds

, Volume 50, Issue 4, pp 589–593 | Cite as

1,5-DI-O-Isoferuloylquinic Acid and Other Phenolic Compounds from Pollen of Calendula officinalis

  • D. N. OlennikovEmail author
  • N. I. Kashchenko
Article

A new phenylpropanoid that was identified as 1,5-di-O-isoferuloylquinic acid (1) and 17 known compounds including 1,5-di-O-feruloylquinic acid (2), which was obtained for the first time from a plant and was synthesized previously, were isolated from pollen of Calendula officinalis. Compounds 1 and 2 were the dominant phenolic compounds from pollen of C. officinalis. It was found that 1 possessed pronounced inhibitory activity against tyrosinase (IC50 11.26 μg/mL).

Keywords

Calendula officinalis Asteraceae 1,5-di-O-isoferuloylquinic acid anti-tyrosinase activity 

Notes

Acknowledgment

The work was supported financially by the SB RAS program “Centers of New Medical Technologies.”

References

  1. 1.
    B. Ylstra, J. Bussher, J. Franken, P. C. H. Hollman, and J. N. M. Mol, Plant J., 6, 201 (1994).CrossRefGoogle Scholar
  2. 2.
    O. M. Andersen and K. R. Markham (eds.), Flavonoids. Chemistry, Biochemistry and Application, Taylor & Francis Group, Boca Raton, London, New York, 2006, pp. 414-415.Google Scholar
  3. 3.
    S. Meenatchisundaram, G. Parameswari, T. Subbraj, T. Suganya, and A. Michael, Ethnobot. Leaflets, 13, 51 (2009).Google Scholar
  4. 4.
    N. Kuhnert, R. Jaiswal, M. F. Matei, T. Sovdat, and S. Deshpande, Rapid Commun. Mass Spectrom., 24, 1575 (2010).PubMedCrossRefGoogle Scholar
  5. 5.
    F. Teramachi, T. Koyano, T. Kowithayakorn, M. Hayashi, K. Komiyama, and M. Ishibashi, J. Nat. Prod., 68, 794 (2005).PubMedCrossRefGoogle Scholar
  6. 6.
    P. Wenzl, A. L. Chaves, J. E. Mayer, I. M. Rao, and M. G. Nair, Phytochemistry, 55, 389 (2000).PubMedCrossRefGoogle Scholar
  7. 7.
    G. F. Pauli, F. Poetsch, and A. Nahrstedt, Phytochem. Anal., 9, 177 (1998).CrossRefGoogle Scholar
  8. 8.
    J. H. Grabber, P. F. Schatz, H. Kim, F. Lu, and J. Ralph, BMC Plant Biol., 10,114 (2010).PubMedCrossRefPubMedCentralGoogle Scholar
  9. 9.
    T. De Paulis, D. E. Schmidt, A. K. Bruchey, M. T. Kirby, M. P. McDonald, P. Commers, D. M. Lovinger, and P. R. Martin, Eur. J. Pharmacol., 442, 215 (2002).PubMedCrossRefGoogle Scholar
  10. 10.
    Y.-J. Yang, X. Liu, H.-R. Wu, X.-F. He, Y.-R. Bi, Y. Zhu, and Z.-L. Liu, Food Chem., 138, 2057 (2013).PubMedCrossRefGoogle Scholar
  11. 11.
    M. N. Clifford, W. Zheng, and N. Kuhnert, Phytochem. Anal., 17, 384 (2006); T. Carbonara, R. Pascale, M. P. Argentieri, P. Papadia, F. P. Fanizzi, L. Villanova, and P. Avato, J. Pharm. Biomed. Anal., 62, 79 (2012).Google Scholar
  12. 12.
    D. N. Olennikov and N. I. Kashchenko, Chem. Nat. Compd., 49, 717 (2013).Google Scholar
  13. 13.
    D. N. Olennikov and N. I. Kashchenko, Sci. World J., 2014, art. ID 654193 (2014).Google Scholar
  14. 14.
    S. Gong, M. Yin, and Z. Yun, J. Cosmet. Sci., 64, 235 (2013).PubMedGoogle Scholar
  15. 15.
    V. A. Kurkin, Chem. Nat. Compd., 39, 123 (2003).CrossRefGoogle Scholar
  16. 16.
    D. N. Olennikov, L. M. Tankhaeva, and S. V. Agafonova, Appl. Biochem. Microbiol., 47, 419 (2011).CrossRefGoogle Scholar
  17. 17.
    L. Lin and J. M. Harnly, J. Agric. Food. Chem., 56, 10105 (2008).PubMedCrossRefGoogle Scholar
  18. 18.
    A. Sakushima, S. Hisada, Y. Ogihara, and S. Nishibe, Chem. Pharm. Bull., 28, 1219 (1980).CrossRefGoogle Scholar
  19. 19.
    N. F. Komissarenko, V. T. Chernobai, and A. I. Derkach, Chem. Nat. Compd., 24, 675 (1988).CrossRefGoogle Scholar
  20. 20.
    D. N. Olennikov and V. V. Partilkhaev, J. Planar Chromatogr.—Mod. TLC, 25, 30 (2012).CrossRefGoogle Scholar
  21. 21.
    E. Vidal-Ollivier, R. Elias, F. Faure, A. Babadjamian, F. Crespin, G. Balansard, and G. Boudon, Planta Med., 55, 73 (1989).PubMedCrossRefGoogle Scholar
  22. 22.
    G. G. Zapesochnaya, S. Z. Ivanova, S. A. Medvedeva, and N. A. Tyukavkina, Chem. Nat. Compd., 14, 156 (1978).CrossRefGoogle Scholar
  23. 23.
    I. Kubo, Q.-X. Chen, K.-I. Nihei, J. S. Calderon, and C. L. Cespedes, Z. Naturforsch., C: J. Biosci., 58, 713 (2003).Google Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  1. 1.Institute of General and Experimental Biology, Siberian BranchRussian Academy of SciencesUlan-UdeRussia

Personalised recommendations