Skip to content
Licensed Unlicensed Requires Authentication Published by De Gruyter (O) October 18, 2016

Self-Association of Glycyrrhizic Acid. NMR Study

  • Svetlana S. Petrova , Anna A. Schlotgauer , Alexander I. Kruppa EMAIL logo and Tatyana V. Leshina

Abstract

The use of various NMR techniques allows to demonstrate the aggregation processes of β-glycyrrhizic acid (GA) in water/methanol (4:1, v:v) mixture with solution pH≤5. The micelle formation was monitored by measuring T2 relaxation and diffusion of GA. The model of gelation from micelles was suggested. It was shown that NMR chemical shifts of the protons of GA glucuronic moiety are sensitive to solution pH and not sensitive to GA concentration changes. At the same time the protons of triterpene moiety are sensitive to the nearest environment during the GA aggregation, and micelles are formed by hydrophobic interaction between the triterpene moieties of GA.


Dedicated to: Kev Salikhov on the occasion of his 80th birthday.


Acknowledgements

This publication is supported by grant 15-04-02538 from the Russian Foundation for Basic Research.

References

1. G. A. Tolstikov, L. A. Baltina, E. E. Schults, A. G. Pokrovsky, Bioorg. Chem. 23 (1997) 691.Search in Google Scholar

2. C. Fiore, M. Eisenhut, E. Ragazzi, G. Zanchin, D. Armanini, J. Ethnopharmacol. 99 (2005) 317.10.1016/j.jep.2005.04.015Search in Google Scholar PubMed PubMed Central

3. A. Otsuka, Y. Yonezawa, K. Iba, T. Tatsumi, H. Sunada, Yakugaku Zasshi 96 (1976) 203.10.1248/yakushi1947.96.2_203Search in Google Scholar PubMed

4. M. Kondo, H. Minamino, G. Okuyama, K. Honda, H. Nagasawa, Y. Otani, J. Soc. Cosmet. Chem. 37 (1986) 177.Search in Google Scholar

5. K. Matsuoka, R. Miyajima, Y. Ishida, S. Karasawa, T. Yoshimura, Colloid Surface A 500 (2016) 112.10.1016/j.colsurfa.2016.04.032Search in Google Scholar

6. N. E. Polyakov, T. V. Leshina, Open Conf. Proc. J. 2 (2011) 64.10.2174/2210289201102010064Search in Google Scholar

7. L. Shi, C. Tang, Ch. Yin, Biomaterials 33 (2012) 7594.10.1016/j.biomaterials.2012.06.072Search in Google Scholar PubMed

8. G. A. Tolstikov, Yu. I. Murinov, L. A. Baltina, M. Yu. Saitova, F. Ch. Zaurdi, V. A. Davydova, D. N. Lazareva, Pharm. Chem. J. 25 (1991) 197.10.1007/BF00772022Search in Google Scholar

9. Y. Yonezawa, A. Otsuka, Yakugaku Zasshi 101 (1981) 829.10.1248/yakushi1947.101.9_829Search in Google Scholar

10. Yu. I. Ragino, V. A. Vavilin, N. F. Salakhutdinov, S. I. Makarova, E. M. Stakhneva, O. G. Safronova, Yu. P. Nikitin, G. A. Tolstikov, Bull. Exp. Biol. Med. 145 (2008) 317.10.1007/s10517-008-0079-5Search in Google Scholar PubMed

11. V. A. Vavilin, N. F. Salakhutdinov, Yu. I. Ragino, N. E. Polyakov, M. B. Taraban, T. V. Leshina, E. M. Stakhneva, V. V. Lyakhovich, Yu. P. Nikitin, G. A. Tolstikov, Biochem. (Mosc.) Suppl. Ser. B Biomedical Chem. 2 (2008) 373.10.1134/S1990750808040070Search in Google Scholar

12. M. Stojančević, N. Pavlović, S. Goločorbin-Kon, M. Mikov, Front. Life Sci. 7 (2013) 112.10.1080/21553769.2013.879925Search in Google Scholar

13. N. E. Polyakov, T. V. Leshina, N. F. Salakhutdinov, L. D. Kispert, J. Phys. Chem. B 110 (2006) 6991.10.1021/jp056038lSearch in Google Scholar PubMed

14. V. S. Kornievskaya, A. I. Kruppa, T. V. Leshina, J. Incl. Phenom. Macrocycl. Chem. 60 (2008) 123.10.1007/s10847-007-9360-xSearch in Google Scholar

15. E. Tykarska, Z. Dutkiewicz, D. Baranowski, Z. Gdaniec, M. Gdaniec, Cryst. Growth Des. 14 (2014) 5871.10.1021/cg5010962Search in Google Scholar

16. I. A. Muraviev, G. S. Bashura, T. G. Krasova, Pharmacy 23 (1974) 14 (in Russian).Search in Google Scholar

17. H. Yoshioka, K. Honda, M. Kondo, J. Colloid Interface Sci. 93 (1983) 540.10.1016/0021-9797(83)90438-1Search in Google Scholar

18. E. Tykarska, S. Sobiak, M. Gdaniec, Cryst. Growth Des. 12 (2012) 2133.10.1021/cg300160cSearch in Google Scholar

19. V. S. Kornievskaya, A. I. Kruppa, N. E. Polyakov, T. V. Leshina, J. Phys. Chem. B 111 (2007) 11447.10.1021/jp0739770Search in Google Scholar

20. J. Spěváček, Curr. Opin. Colloid Interface Sci. 14 (2009) 184.10.1016/j.cocis.2008.10.003Search in Google Scholar

21. M. V. Badiger, P. R. Rajamohanan, M. G. Kulkarni, S. Ganapathy, R. A. Mashelkar, Macromolecules 24 (1991) 106.10.1021/ma00001a017Search in Google Scholar

22. E. Díez-Peña, I. Quijada-Garrido, J. M. Barrales-Rienda, M. Wilhelm, H. W. Spiess, Macromol. Chem. Phys 203 (2002) 491.10.1002/1521-3935(20020201)203:3<491::AID-MACP491>3.0.CO;2-1Search in Google Scholar

23. M. V. Popova, Y. S. Tchernyshev, D. Michel, Langmuir 20 (2004) 632.10.1021/la035465sSearch in Google Scholar

24. B. Jönsson, B. Lindman, K. Holmberg, B. Kronberg, Surfactants and polymers in aqueous solution, Wiley, Chichester, UK, 1998, p. 438.Search in Google Scholar

25. Y. Hanzhen, D. Youru, Zh. Sui, Y. Jiayong, Sci. China (Series A), 42 (1999) 319.10.1007/BF02879067Search in Google Scholar

26. M. V. Zelikman, A. V. Kim, N. N. Medvedev, O. Yu. Selyutina, N. E. Polyakov, J. Struct. Chem. 56 (2015) 67.10.1134/S0022476615010102Search in Google Scholar

27. V. N. Gusakov, V. N. Maistrenko, P. P. Safiullin, Russ. J. Gen. Chem. 71 (2001) 1307.10.1023/A:1013297601183Search in Google Scholar

Received: 2016-6-28
Accepted: 2016-9-10
Published Online: 2016-10-18
Published in Print: 2017-4-1

©2017 Walter de Gruyter GmbH, Berlin/Boston

Downloaded on 13.5.2024 from https://www.degruyter.com/document/doi/10.1515/zpch-2016-0845/html
Scroll to top button