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Host–guest complexation in the β-glycyrrhizic acid–2,8-dimethyl-5-[2´-(6″-methylpyridin-3″-yl)ethyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole system

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Abstract

Electronic, IR, and NMR spectroscopy methods were used to study the interaction in the β-glycyrrhizic acid (GA)–2,8-dimethyl-5-[2´-(6″-methylpyridin-3″-yl)ethyl]-2,3,4,5-tetra-hydro-1H-pyrido[4,3-b]indole (Dim) system in an alcoholic medium. The complete assignment of signals in the 1H and 13C NMR spectra of Dim and GA in CD3OD was made for the individual components and for thier mixtures at different ratios. These data suggest the formation of a host–guest complex in this system. It is hypothesized that associates of GA molecules interact with Dim through Δ12,13–carbonyl group conjugated bonds in the triterpene moiety of GA that interact with the aromatic systems of the indole and pyridine moieties of Dim, as well as via an acid-base mechanism involving mainly the carboxy groups of glucuronic acid residues in the carbohydrate part of GA and the nitrogen atom of the tetrahydropyridine ring of Dim.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Research Center of the Russian Academy of Sciences, 71 prosp. Oktyabrya, 450054, Ufa, Russian Federation

    I. G. Konkina, O. V. Shitikova, A. N. Lobov & Yu. I. Murinov

  2. Institute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severnyi proezd, 142432, Chernogolovka, Moscow Region, Russian Federation

    S. O. Bachurin

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  1. I. G. Konkina
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  2. O. V. Shitikova
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  3. A. N. Lobov
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  4. Yu. I. Murinov
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  5. S. O. Bachurin
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Correspondence to I. G. Konkina.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1385–1393, June, 2015.

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Konkina, I.G., Shitikova, O.V., Lobov, A.N. et al. Host–guest complexation in the β-glycyrrhizic acid–2,8-dimethyl-5-[2´-(6″-methylpyridin-3″-yl)ethyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole system. Russ Chem Bull 64, 1385–1393 (2015). https://doi.org/10.1007/s11172-015-1021-4

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  • DOI: https://doi.org/10.1007/s11172-015-1021-4

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