The reaction of dihydroquercetin monosuccinate with ammonia, a series of alkylamines, and amino-derivatives of heterocyclic compounds including nitroxyl radicals and alkaloids produced the corresponding ionic conjugates, the water solubility of which was 1–2 orders of magnitude greater than that of dihydroquercetin with retention of the high antioxidant activity.
Similar content being viewed by others
References
A. Gaspar, M. J. Matos, J. Garrido, E. Uriarte, and F. Borges, Chem. Rev., 114, 4960 (2014); C. F. M. Silva, D. C. G. A. Pinto, and A. M. S. Silva, ChemMedChem., 11, 2252 (2016); R. S. Keri, S. Budagumpi, R. Krishna Pai, and R. G. Balakrishna, Eur. J. Med. Chem., 78, 340 (2014); S. Emani and Z. Ghanbarimasir, Eur. J. Med. Chem., 93, 539 (2015).
M. P. Koroteev, A. O. Pozdeev, A. M. Koroteev, G. Z. Kaziev, A. T. Teleshev, and E. N. Ofitserov, Butler. Soobshch., 39, 94 (2014); E. V. Nifant’ev, A. M. Koroteev, A. O. Pozdeev, M. P. Koroteev, and E. N. Rassadkina, Dokl. Akad. Nauk, 459, 567 (2014).
N. V. Kosheleva, E. I. Chernyak, S. V. Morozov, V. I. Vinogradova, Sh. Sh. Sagdullaev, N. D. Abdullaev, and I. A. Grigor’ev, Chem. Nat. Compd., 50, 443 (2014).
N. V. Kosheleva, E. I. Chernyak, Yu. F. Polienko, S. V. Morozov, and I. A. Grigor’ev, Chem. Nat. Compd., 50, 261 (2014).
Sh. N. Zhurakulov, V. A. Babkin, E. I. Chernyak, S. V. Morozov, I. A. Grigor’ev, M. G. Levkovich, and V. I. Vinogradova, Chem. Nat. Compd., 51, 57 (2015).
Yu. V. Yushkova, E. I. Chernyak, S. V. Morozov, and I. A. Grigor’ev, Chem. Nat. Compd., 51, 1070 (2015); Yu. V. Yushkova, S. V. Morozov, E. I. Chernyak, and I. A. Grigor’ev, Chem. Nat. Compd., 52, 1015 (2016).
R. Braatz, K. Gorler, G. Halbach, H. Soicke, and K. Schmidt, UK Patent 2,167,414A, May 29, 1986.
Yu. V. Yushkova, E. I. Chernyak, S. V. Morozov, and I. A. Grigor’ev, Chem. Nat. Compd., 50, 827 (2014).
B. N. Finkel’shtein, O. S. Danilovtseva, B. N. Bazhenov, and M. Yu. Saibotalov, in: Proceedings of the All-Russian Scientific Conference “Biotechnology of Plant Raw Material, Quality and Safety of Food Products” [in Russian], Irkutsk, 2010, p. 79.
E. E. Nifant’ev, M. P. Koroteev, G. Z. Kaziev, A. A. Umanskii, A. A. Grachev, V. M. Men’shov, Yu. E. Tsvetkov, N. E. Nifant’ev, V. K. Belskii, and A. I. Stash, Zh. Obshch. Khim., 76, 164 (2006); E. Kiehlmann, K. Biradha, K. V. Domasevitch, and M. J. Zaworotko, Can. J. Chem., 77, 1436 (1999).
M. Toshiyuki and C. Yenyang, JP Patent 2008007449 A, Jan. 17, 2008.
I. A. Grigor’ev, N. I. Tkacheva, and S. V. Morozov, Curr. Med. Chem., 21, 2839 (2014).
R. M. Silverstein, G. C. Bassler, and T. C. Morrill, Spectrometric Identification of Organic Compounds, 3rd Ed., Wiley, New York (1974), 340 pp. [Russian translation, Mir, Moscow, 1977, pp. 183–185].
Yu. V. Yushkova, E. I. Chernyak, Yu. F. Polienko, Yu. V. Gatilov, S. V. Morozov, and I. A. Grigor’ev, Chem. Nat. Compd., 49, 253 (2013); A. N. Antimonova, N. I. Petrenko, E. E. Shul’ts, Yu. F. Polienko, M. M. Shakirov, I. G. Irtegova, M. A. Pokrovskii, K. M. Sherman, I. A. Grigorev, A. G. Pokrovskii, and G. A. Tolstikov, Bioorg. Khim., 39, 206 (2013).
The Sadtler Standard Carbon-13 NMR Spectra. Sadtler Research Laboratories, USA; NMR Spectra Database of the University of Wisconsin-Madison Laboratory, G. Reich; http://www.chem.wisc.edu/areas/reich/chem605/index.htm
Y. Zu, W. Wu, X. Zhao, Y. Li, W. Wang, C. Zhong, Y. Zhang, and X. Zhao, Int. J. Pharm., 471, 366 (2014).
State Pharmacopoeia of the Russian Federation, Izd. Nauchnyi Tsentr Ekspertizy Sredstv Meditsinskogo Primeneniya, Moscow, 2008, p. 92.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2017, pp. 889–894.
Rights and permissions
About this article
Cite this article
Mamontova, N.V., Chernyak, E.I., Amosov, E.V. et al. First Ionic Conjugates of Dihydroquercetin Monosuccinate with Amines. Chem Nat Compd 53, 1045–1051 (2017). https://doi.org/10.1007/s10600-017-2198-6
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10600-017-2198-6