Amino-acid conjugates of glycyrrhizic acid (GA) containing phenylalanine, tyrosine, and tryptophan in the carbohydrate and triterpene parts were synthesized using N-hydroxybenzotriazole (HOBt)-N,N′-dicyclohexylcarbodiimide (DCC) and sodium salts of the amino acids. GA conjugates containing two aminoacid residues in the glycoside carbohydrate part were synthesized using N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline. The GA conjugate with tyrosine exhibited weak but consistent antiviral activity against flu virus A/St.-Petersburg/05/09 (H1N1)pdm09 that was similar to the standard strain A/California/07/09 and pronounced antiviral activity against respiratory-syncytial virus (RSV) and herpes simplex virus (HSV-1).
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
G. A. Tolstikov, L. A. Baltina, V. P. Grankina, R. M. Kondratenko, and T. G. Tolstikova, Licorice: Biodiversity, Chemistry, and Medical Application [in Russian], Akad. Izd. Geo. Novosibirsk, 2007, 311 pp.
G. Hoever, L. Baltina, M. Michaelis, R. Kondratenko, L. Baltina, G. Tolstikov, H. W. Doerr, and J. Cinatl, Jr., J. Med. Chem., 48, 1256 (2006).
J.-Ch. Lin, J.-M. Cherng, M.-Sh. Hung, L. A. Baltina, L. Baltina, and R. Kondratenko, Antiviral Res., 79, 6 (2008).
L. A. Baltina, Jr., R. M. Kondratenko, L. A. Baltina, N. Z. Baschenko, and O. A. Plyasunova, Russ. J. Bioorg. Chem., 35, 510 (2009).
L. A. Baltina, Jr., O. V. Stolyarova, L. A. Baltina, R. M. Kondratenko, V. A. Fedorova, Ya. A. Orshanskaya, and V. V. Zarubaev, Chem. Nat. Compd., 50, 317 (2014).
L. A. Baltina, V. V. Zarubaev, L. A. Baltina, I. A. Orshanskaya, A. I. Fairushina, O. I. Kiselev, and M. S. Yunusov, Bioorg. Med. Chem. Lett., 25, 1742 (2015).
L. A. Baltina, S. A. Ryzhova, E. V. Vasil’eva, G. A. Tolstikov, G. M. Sakhautdinova, and F. S. Zarudii, Bioorg. Khim., 20 (12), 1365 (1994).
L. A. Baltina, S. A. Ryzhova, E. V. Vasil’eva, and G. A. Tolstikov, Bioorg. Khim., 20 (1), 55 (1994).
L. A. Baltina, A. I. Fairushina, and L. A. Baltina, Russ. J. Gen. Chem., 85, 2735 (2015).
L. A. Baltina, O. Kunert, A. A. Fatykhov, R. M. Kondratenko, L. V. Spirikhin, L. A. Baltina, Jr., F. Z. Galin, G. A. Tolstikov, and E. Haslinger, Chem. Nat. Compd., 41, 432 (2005).
A. M. Mironov et al. (eds.), Handbook for Preclinical Drug Trials [in Russian], Part 1, Grif i K, Moscow, 2012, 944 pp.
A. J. Gordon and R. A. Ford, The Chemist's Companion, Wiley-Interscience, New York (1972) [Russian translation, Mir, Moscow, 1976, 541 pp.].
O. V. Stolyarova, L. A. Baltina, Jr., L. R. Mikhailova, T. M. Gabbasov, L. A. Baltina, and G. A. Tolstikov, Khim. Interesakh Ustoich. Razvit., 16, 571 (2008).
E. Borenfreund, H. Babich, and N. Martin-Alguacil, Toxicol. in Vitro, 2, 1 (1988).
Acknowledgment
The work was supported financially by the RSF (Grant 14-03-01307).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2017, pp. 932–935.
Rights and permissions
About this article
Cite this article
Baltina, L.A., Fairushina, A.I., Baltina, L.A. et al. Synthesis and Antiviral Activity of Glycyrrhizic-Acid Conjugates with Aromatic Amino Acids. Chem Nat Compd 53, 1096–1100 (2017). https://doi.org/10.1007/s10600-017-2209-7
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10600-017-2209-7