Synthesis and study of complexes of the novel Russian antiviral drug Camphecene with pentacyclic triterpenes of licorice

S. S. Khizrieva; E. V. Vetrova; S. N. Borisenko; E. V. Maksimenko; N. I. Borisenko

doi:10.15826/chimtech.2020.7.4.10

Synthesis and study of complexes of the novel Russian antiviral drug Camphecene with pentacyclic triterpenes of licorice

S. S. Khizrieva, E. V. Vetrova, S. N. Borisenko, E. V. Maksimenko, N. I. Borisenko

Abstract

For the first time, the complexation of pentacyclic triterpenes of licorice (glycyrrhizic acid (GA) and its aglycone, glycyrrhetinic acid (GLA)) with the novel Russian antiviral drug Camphecene (Camph) was investigated. The complexes obtained at different molar ratios were studied using both UV/Vis spectroscopy and mass spectrometry (ESI MS). Formation of the host:guest complexes were registered: GA and GLA molecular complexes (Camph+2GA; Camph+2GLA) with stability constants К = 6.94 10⁶ М^-2 and К = 2.89 10⁶ М^-2, respectively. The research results demonstrate a considerable potential of ESI MS as a technique for simple and fast detection of formation of the complexes of GA /GLA and the novel drugs.

Keywords

Camphecene; glycyrrhizic acid; glycyrrhetinic acid; antiviral activity; supramolecular complexes

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References

Zarubaev VV, Anikin VB, Smirnov VS. Anti-viral activity of glycyrrhetinic and glycyrrhizic acids. Rus J of Inf and Imm = Infektsiyaiimmunitet. 2016;6(3):199–206. doi:10.15789/2220-7619-20163-199-206

Akram M, Tahir IM, Shah SMA, Mahmood Z, Altaf A, Ahmad K, Munir N, Daniyal M, Nasir S, Mehboob H. Antiviral potential of medicinal plants against HIV, HSV, influenza, hepatitis, and coxsackievirus: A systematic review. Phytother Res. 2018;32(5):811–22. doi:10.1002/ptr.6024

Dhama K, Karthik K, Khandia R, Munjal A, Tiwari R, Rana R, Khurana SK, Sana U, Khan RU, Alagawany M, Farag MR., Dadar M, Joshi SK. Medicinal and Therapeutic Potential of Herbs and Plant Metabolites / Extracts Countering Viral Pathogens - Current Knowledge and Future Prospects. Curr Drug Metab. 2018;19(3):236–63. doi:10.2174/1389200219666180129145252

Tolstikov GA, Shultz EE, Baltina LA, PokrovskyAG. Glycyrrhizicacid. Rus J of Bioorg Chem [Internet]. 1997;23(9):625–42. Available from: https://europepmc.org/article/med/9441592

Shibata SA. Drug over the millennia: Pharmacognosy, chemistry, and pharmacology of licorice. J YakugakuZasshi. 2000;120(10):849–62. doi:10.1248/yakushi1947.120.10_849

Astafyeva OV, Sukhenko LT, Egorov MA. [Antibacterial activity of extracted biologically active substances and extracts of roots of Glycyrrhiza glabra L]. Khimiya rastitel’nogo syr’ya [Chemistry of raw plant materials]. 2013;(3):261–3. Russian. doi:10.14258/jcprm.1303261

Yang R, Wang LQ, Yuan BC, Liu Y. The pharmacological activities of Licorice. Planta Med. 2015;81(18):1654–69. doi:10.1055/s-0035-1557893

Pompei R, Flore O, Marccialis MA, Pani A, Loddo B. Glycyrrhizic acid inhibits virus growth and inactivates virus particles. Nature. 1979;281:689–90. doi:10.1038/281689a0

Hussain H, Green IR, Shamraiz U, Saleem M, Badshah A, Abbas G, Rehman NU, Irshad M. Therapeutic potential of glycyrrhetinic acids: a patent review (2010-2017). Expert Opin. Ther. Pat. 2018;28(5):383–98. doi:10.1080/13543776.2018.1455828

Baltina LA, Kondratenko RM, Baltina JR, Plyasunova OA, Pokrovskii AG, Tolstikov GA. Search for new drugs: Prospects for the creation of new antiviral drugs based on glycyrrhizic acid and its derivatives. Pharm Chem J. 2009;43(10):539–48. doi:10.1007/s11094-010-0348-2

Singh L, Indermun S, Govender M, Kumar P, du Toit LC, Choonara YE, Pillay V. Drug Delivery Strategies for Antivirals against Hepatitis B Virus. Viruses. 2018;10(5):E267. doi:10.3390/v10050267

Tolstikova TG, Tolstikov AG, Tolstikov GA. On the way to low-dose medicines. Herald of the Russian Academy of Sciences. 2007;77(10):447–53. doi:10.1134/S1019331607050012

Vetrova EV, Borisenko NI, Lekar' AV, Maksimenko EV, Borisenko SN, Khizrieva SS. [Mass spectrometry of glycyrrethenic acid complexes with striptomycines]. Khimiya rastitel’nogo syr’ya [Chemistry of raw plant materials]. 2019;(1):119–26. doi:10.14258/jcprm.2019013319

Zarubaev VV, Garshinina AV, Tretiak TS, Fedorova VA,Shtro AA, Sokolova AS, YarovayaOI, Salakhutdinov NF. Broad range of inhibiting action of novel Camphor-based compound with anti-hemagglutinin activity against influenza viruses in vitro and in vivo. Antiviral Res. 2015;120:126–33. doi:10.1016/j.antiviral.2015.06.004

Vavilin VA, Salakhutdinov NF,RaginoYuI, Polyakov NE, Taraban MB, Leshina TV, Stakhneva EM, Lyakhovich VV, NikitinYuP, Tolstikov GA. The Cholesterol Lowering Properties of the Complex Compound Simvastatin with Glycyrrhizic Acid (Simvaglyzin) in Experimental Models. Biochem (Moscow) Suppl Series B: Biomed Chem. 2008;2(4):373–80. doi:10.1134/S1990750808040070

DOI: https://doi.org/10.15826/chimtech.2020.7.4.10

Copyright (c) 2020 S. S. Khizrieva, E. V. Vetrova, S. N. Borisenko, E. V. Maksimenko, N. I. Borisenko

This work is licensed under a Creative Commons Attribution 4.0 International License.

Chimica Techno Acta, 2014-2024
ISSN 2411-1414 (Online)
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