Biopolym. Cell. 2012; 28(1):62-67.
http://dx.doi.org/10.7124/bc.00002E
Bioorganic Chemistry
Molecular complexes of the triterpene glycosides with L-tyrosine and their biological activity
1Yakovishin L. A., 2Lekar A. V., 3Vetrova E. V., 2Borisenko N. I., 3Borisenko S. N., 4Grishkovets V. I.
  1. Sevastopol National Technical University
    33, Universytetska Str., Sevastopol, Ukraine, 99053
  2. Ecological and Analytical Center, Southern Federal University
    7, Zorge Str., Rostov-on-Don, Russian Federation, 344090
  3. The Resesarch Institute of Physical and Organic Chemistry, Southern Federal University
    194/2, pr. Stachki, Rostov-on-Don, Russian Federation, 344090
  4. Taurida National V. I. Vernadsky University
    4, pr. Vernadsky, 4, Simferopol, Ukraine, 95007

Abstract

Aim. To investigate the complexation of L-tyrosine (Tyr) with hederagenin 3-O-α-L-rhamnopyranosyl-(1→2)-O-α-Larabinopyranoside (α-hederin) and its 28-O-α-L-rhamnopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester (hederasaponin C); to study the effect of glycosides, Tyr, and their mixtures on Avena sativa L. seed germination. Methods. Electrospray ionization mass spectrometry. Results. Mass spectra of mixes of glycosides with Tyr have been received and interpreted. The comparative analysis of biological activity of individual glycosides and their complexes with Tyr and others aromatic amino acids has been performed. Conclusions. For the first time a composition of the complexes is established by mass spectrometry. The complex of hederin with Tyr has appeared most toxic.
Keywords: &alpha-hederin, hederasaponin C, L-tyrosine, complexation, mass spectrometry, Avena sativa L.
Full text: (PDF, in English) (PDF, in Russian)

References

[1] Tolstikova T. G., Bryzgalov A. O., Sorokina I. V., Ratushnyak A. S., Zapara T. A., Simonova O. G., Tolstikov G. A. To the nature of the effect of glycosidic clathration of pharmacons. Dokl. Biol. Sci 2007 416:336–337.
[2] Tolstikova T. G., Tolstikov A. G., Tolstikov G. A. On the way to low-dose drugs. Vestn. Ross. Akad. Nauk 2007 77, N 10:867–874.
[3] Polyakov N. E., Khan V. K., Taraban M. B., Leshina T. V., Salakhutdinov N. F., Tolstikov G. A. Complexation of lappaconitine with glycyrrhizic acid: stability and reactivity studies. J. Phys. Chem. B 2005 109, N 51:24526–24530.
[4] Polyakov N. E., Leshina T. V. Glycyrrhizic acid as a novel drug delivery vector: synergy of drug transport and efficacy. Open Conf. Proc. J 2011 2:64–72.
[5] Hu Y. J., Liu Y., Wang J. B., Xiao X. H., Qu S. S. Study of the interaction between monoammonium glycyrrhizinate and bovine serum albumin. J. Pharm. Biomed. Anal 2004 36, N 4:915–919.
[6] Lee P. S., Han J. Y., Song T. W., Sung J. H., Kwon O. S., Song S., Chung Y. B. Physicochemical characteristics and bioavailability of a novel intestinal metabolite of ginseng saponin (IH901) complexed with beta-cyclodextrin. Int. J. Pharm 2006 316, N 1–2:29–36.
[7] Polyakov N. E., Leshina T. V., Salakhutdinov N. F., Konovalova T. A., Kispert L. D. Antioxidant and redox properties of supramolecular complexes of carotenoids with beta-glycyrrhizic acid. Free Radic. Biol. Med 2006 40, N 10:1804–1809.
[8] Polyakov N. E., Leshina T. V., Salakhutdinov N. F., Kispert L. D. Host-guest complexes of carotenoids with beta-glycyrrhizic acid. J. Phys. Chem. B 2006 110, N 13:6991–6998.
[9] Polyakov N. E., Khan V. K., Taraban M. B., Leshina T. V. Complex of calcium receptor blocker nifedipine with glycyrrhizic acid. J. Phys. Chem. B 2008 112, N 14:4435–4440.
[10] Pilipenko V. V., Sukhodub L. F., Aksyonov S. A., Kalinkevich A. N., Kintia P. K. 252Cf plasma desorption mass spectrometric study of interactions of steroid glycosides with amino acids. Rapid Commun. Mass Spectrom 2000 14, N 10:819–823.
[11] Pilipenko V. V., Sukhodub L. F. Mass spectrometry study of plant steroid glycosides and their interactions with biomolecules. Biopolym. Cell 2002 18, N 2:139–141.
[12] Pilipenko V. V., Aksyonov S. A., Kalinkevich A. N., Sukhodub L. F. PDMS study of the steroid glycosides interaction with amino acids. Biopolym. Cell 2000 16, N 3:212–219.
[13] Gorchakova N. A., Samarskaya T. G., Samarsky V. A., Lezina G. G., Grischenko L. I., Babak V. V. Complexation of cardiac glycosides with amino acids and alkaline earth metals. Eksp. Klin. Farmakol 1992 55, N 2:106–109.
[14] Tolstikov G. A., Baltina L. A., Grankina V. P., Kondratenko R. M., Tolstikova T. G. Licorice: biodiversity, chemistry and application in medicine Novosibirsk: Geo, 2007 311 p.
[15] Yakovishin L. A., Grishkovets V. I., Schroeder G., Borisenko N. I. Molecular complexation of ivy saponins with some drugs and biologically active substances. Functionalized molecules – synthesis, properties and application / Ed. V. I. Rybachenko Donetsk: Schidnyj wydawnyczyj dim, 2010 Chapter 4:85–103.
[16] Hostettmann K., Marston A. Saponins Cambridge: Univ. press, 2005 564 p.
[17] Shashkov A. S., Grishkovets V. I., Loloyko A. A., Chirva V. Ya. Triterpene glycosides of Hedera taurica I. Structure of tauroside E from the leaves of Hedera taurica. Khim. Prir. Soedin 1987 N 3:363–366.
[18] Grishkovets V. I., Sidorov D. Yu., Yakovishin L. A., Arnautov N. N., Shashkov A. S., Chirva V. Ya. Triterpene glycosides of Hedera canariensis I. Structures of glycosides L-A, L-B1, L-B2, L-C, L-D, L-E1, L-G1, L-G2, L-G3, L-G4, L-H1, L-H2, and L-I1 from the leaves of Hedera canariensis. Khim. Prir. Soedin 1996 N 3:377–383.
[19] Mshvildadze V., Elias R., Faure R., Rondeau D., Debrauwer L., Dekanosidze G., Kemertelidze E., Balansard G. Triterpenoid saponins from the leaves of Hedera pastuchowii. Chem. Pharm. Bull 2004 52, N 12:1411–1415.
[20] Mshvildadze V., Elias R., Faure R., Debrauwer L., Dekanosidze G., Kemertelidze E., Balansard G. Triterpenoid saponins from berries of Hedera colchica. Chem. Pharm. Bull 2001 49, N 6:752–754.
[21] Elias R., Diaz-Lanza A. M., Vidal-Ollivier E., Balansard G., Faure R., Babadjamian A. Triterpenoid saponins from the leaves of Hedera helix. J. Nat. Prod 1991 54, N 1:98–103.
[22] Buechi S., Bolli R. Efeu – expektorans, mukolytikum und broncholytikum. Botanische und klinische aspekte. Phytotheraphie 2003 N 3:19–22.
[23] Lekar A. V., Vetrova E. V., Borisenko N. I., Yakovishin L. A., Grishkovets V. I., Borisenko S. N. Electrospray ionization mass spectrometry of mixtures of triterpene glycosides with L-phenylalanine. J. Appl. Spectrosc 2011 78, N 4:501–505.
[24] Yakovishin L. A., Lekar A. V., Vetrova E. V., Borisenko N. I., Grishkovets V. I. Molecular complexes of triterpene glycosides with L-histidine and their biological activity. Biopolym. Cell 2011 27, N 4:300–305.
[25] Yakovishin L. A., Grishkovets V. I., Sergienko U. I., Korzh E. N. Molecular complexation of triterpene glycosides with L-phenylalanine in water solutions. Sci. Notes of TNU. Ser. Biol. Chem 2010 23, (62), N 3:255–261.
[26] Yakovishin L. A., Epishina N. V., Belash D. Yu., Yarovoy I. R., Korzh E. N., Grishkovets V. I. Influence of the triterpene glycosides and their molecular complexes with aromatic amino acid on seeds germination in laboratory. VI Int. Sci.-Tech. conf. «Modern trends in theoretical and applied biophysics, physics and chemistry» (26–30 Apr. 2010, Sevastopol) Sevastopol, 2010 Vol. 1:350–351.
[27] Yakovishin L. A., Grishkovets V. I., Sergienko U. I., Dovgy I. I. Molecular complexation of triterpene glycosides with L-tyrosine in aqueous solutions. Sci. Notes of TNU. Ser. Biol. Chem 2011 24 (63), N 1:232–238.
[28] Podolak I., Galanty A., Sobolewska D. Saponins as cytotoxic agents: a review. Phytochem. Rev 2010 9, N 3:425–474.