Biopolym. Cell. 2011; 27(4):300-305.
Bioorganic Chemistry
Molecular complexes of triterpene glycosides with L-histidine and their biological activity
1Yakovishin L. A., 2Lekar A. V., 3Vetrova E. V., 2Borisenko N. I., 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. Institute of Physical and Organic Chemistry, Southern Federal University
    194/2, Stachka Ave., Rostov-on-Don, Russian Federation, 344090
  4. V. I. Vernadsky Taurida National University
    4, Vernadsky Ave., Simferopol, Crimea, Ukraine, 95007

Abstract

Aim. To investigate the complexation of L-histidine (His) with hederagenin 3-O-α-L-rhamnopyranosyl-(1→2)-O-α-L-arabino pyranoside (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, His, and their mixtures at Avena sativa L. seed germination. Methods. Electrospray ionization mass spectrometry. Results. The mass spectra of glycosides mixed with His are received and interpreted. The comparative analysis of biological activity of individual substances and their complexes is performed. Conclusions. For the first time, the composition of aforesaid complexes is established by mass spectrometry. Complexes have appeared less toxic, than individual glycosides.
Keywords: α-hederin, hederasaponin C, L-histidine, complexation, mass spectrometry, Avena sativa L.

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, N 1 P. 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 P. 867–874.
[3] 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.
[4] Dalimov D. N., Isaev Yu. T., Saiitkulov A. M. Molecular complexes of ammonium glycyrrhizate with certain medicinal agents and their interferon-inducing activity Khim. Prirod. Soed 2001 N 2 P. 132–134.
[5] 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 P. 819–823.
[6] Pilipenko V. V., Sukhodub L. F. Mass spectrometry study of plant steroid glycosides and their interactions with biomolecules Biopolym. Cell 2002 18, N 2 P. 139–141.
[7] Sukhodub L. F., Kalinkevich A. N. Plant steroid glycosides and their complexation with biomolecules (mass-spectrometry data) Zhur. Akad. Med. Nauk Ukr 2009 15, N 2 P. 225–245.
[8] 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 Pharmacol. and Toxicol 1992 N 27 P. 106–109.
[9] Sieben A., Prenner L., Sorkalla T., Wolf A., Jakobs D., Runkel F., Haberlein H. -Hederin, but not hederacoside C and hederagenin from Hedera helix, affects the binding behavior, dynamics, and regulation of 2-adrenergic receptors Biochemistry 2009 48, N 15 P. 3477–3482.
[10] Boltshauser V. Wirkmechanismus von efeu entschlusselt. Efeusaponine entfalten eine b-adrenerge wirkung in den atemwegen Phytotheraphie 2006 N 4 S. 20–22.
[11] Ancuceanu R. V., Istudor V. Pharmacologically active natural compounds for lung cancer Altern. Med. Rev 2004 9, N 4 P. 402–419.
[12] Hostettmann K., Marston A. Saponins Cambrige: Univ. press, 1995 548 p.
[13] Vetrova E. V., Lekar A. V., Yakovishin L. A., Borisenko N. I. Mass spectrometry research of complexes of triterpene glycosides (hederosides) with amino acids X Int. workshop on magnetic resonance (spectroscopy, tomography and ecology) (2–7 Mar. 2010, Rostov-on-Don) Rostov-on-Don, 2010 P. 30.
[14] Mashkovsky M. D. Medicines Kharkov: Torsing, 1997 Vol. 2 592 p.
[15] Yakovishin L. A., Grishkovets V. I., Rubinson M. A., Korzh E. N. The complex's formation of triterpene glycoside a-hederin with hydrophilic proteinogenous amino acids Sci. Notes Taurida V. I. Vernadsky Nat. Univ., ser. Biol. Chem 2009 22, N 1 P. 208–213.
[16] Yakovishin L. A., Borisenko N. I., Rudnev M. I., Vetrova E. V., Grishkovets V. I. Self-association and complexation of triterpene glycosides and cholesterol Khim. Prirod. Soed 2010 N 1 P. 45–48.
[17] Lekar A. V., Vetrova E. V., Borisenko N. I., Yakovishin L. A., Grishkovets V. I. Electrospray ionization mass spectrometry of mixtures of triterpene glycosides with paracetamol Zhur. Priklad. Spektroskop 2010 77, N 5 P. 668–672.
[18] Vetrova E. V., Lekar A. V., Yakovishin L. A., Borisenko N. I. Research of complexes of plants triterpene glycosides from Araliaceae Juss. with medical products X Int. workshop on magnetic resonance (spectroscopy, tomography and ecology) (2–7 Mar. 2010, Rostov-on-Don) Rostov-on-Don, 2010 P. 29.
[19] 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. Prirod. Soed 1987 N 3 P. 363–366.
[20] 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. Prirod. Soed 1996 N 3 P. 377–383.
[21] Anisimov MM, Chirva VYa. About of the biological role of triterpene glycosides Usp Sovrem Biol 1980; 90(3(6)):351-64.
[22] Waller G. R., Jurzysta M., Trohne R. L. Z. Root saponins from alfalfa (Medicago sativa L.) and their allelopathic activity on weeds and wheat Allelopathy J 1995 2, N 1 P. 21–30.
[23] Podolak I., Galanty A., Sobolewska D. Saponins as cytotoxic agents: a review Phytochem. Rev 2010 9 P. 425–474.
[24] 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 Taurida V. I. Vernadsky Nat. Univ., ser. Biol. Chem 2010 23, N 3 P. 255– 261.
[25] Yakovishin L. A., Grishkovets V. I., Epishina N. V., Kurtametov I. S. Molecular complexation of the triterpene glycosides with tryptophan in water solutions Sci. Notes Taurida V. I. Vernadsky Nat. Univ., ser. Biol. Chem 2010 23, N 2 P. 270–275.