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


ABSTRACT: Betulin-3,28-diphosphate (BDP) obtained by phosphorylation of betulin using POCl? 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.

SUBMITTER: Melnikova NB 

PROVIDER: S-EPMC6099732 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature

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

Melnikova Nina B NB   Malygina Darina S DS   Klabukova Irina N IN   Belov Denis V DV   Vasin Viktor A VA   Petrov Pavel S PS   Knyazev Alexander V AV   Markin Alexey V AV  

Molecules (Basel, Switzerland) 20180514 5


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 <sup>13</sup>C and <sup>31</sup>P-NMR spectra, powder XRD experiments, as well as differential scanning calorimetry (DSC) and thermogravimetric analysis (TG) methods. The  ...[more]

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