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Molecules 2018, 23(5), 1175; https://doi.org/10.3390/molecules23051175

Betulin-3,28-diphosphate. Physico-Chemical Properties and In Vitro Biological Activity Experiments

1
Department of Pharmaceutical Chemistry, Privolzhsky Research Medical University, Minin sq., 10/1, 603950 Nizhny Novgorod, Russia
2
Department of Chemistry, N.P. Ogarev Mordovian State University, Bolshevistskaya St. 68, 430005 Saransk, Russia
3
Department of Chemistry, Lobachevsky University, 23/5 Gagarin Av., 603950 Nizhny Novgorod, Russia
*
Author to whom correspondence should be addressed.
Received: 11 April 2018 / Revised: 10 May 2018 / Accepted: 11 May 2018 / Published: 14 May 2018
(This article belongs to the Section Natural Products Chemistry)
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Abstract

Betulin-3,28-diphosphate (BDP) obtained by phosphorylation of betulin using POCl3 has two main structural forms—BDP-1 and BDP-2—which differ in ethanol solubility, melting point, FTIR spectra, thermoanalytical characteristics and biological activity. Betulin-3,28-diphosphate and its sodium salt (Na-BDP) were characterized using 13C and 31P-NMR spectra, powder XRD experiments, as well as differential scanning calorimetry (DSC) and thermogravimetric analysis (TG) methods. The exo-effects at 193 ± 8 °C for ethanol soluble BDP-1 samples (−19.7 ± 0.2 kJ∙mol−1) were about three times less than for ethanol insoluble BDP-2 samples f (−70.5 ± 0.7 kJ∙mol−1). The DSC curves of Na-BDP-1 and Na-BDP-2 characterized the endo-effects having a maximum at 95–112 °C. Water-soluble Na-BDP-1 was obtained as needle-like crystals, unlike poorly crystalline Na-BDP-2, whereas BDP-1 and BDP-2 aged with time and were isolated as amorphous substances. In vitro experiments on rats showed that compared to the control, Na-BDP-1 increased catalase and SOD activity and improved energy metabolism more effectively than Na-BDP-2. View Full-Text
Keywords: betulin-3,28-diphosphate and its sodium salt; thermoanalytical properties; antioxidant activity betulin-3,28-diphosphate and its sodium salt; thermoanalytical properties; antioxidant activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Melnikova, N.B.; Malygina, D.S.; Klabukova, I.N.; Belov, D.V.; Vasin, V.A.; Petrov, P.S.; Knyazev, A.V.; Markin, A.V. Betulin-3,28-diphosphate. Physico-Chemical Properties and In Vitro Biological Activity Experiments. Molecules 2018, 23, 1175.

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