Betulin-3,28-diphosphate. Physico-Chemical Properties and In Vitro Biological Activity Experiments
Abstract
:1. Introduction
2. Results and Discussion
2.1. Properties of the Betulin-3,28-diphosphate
2.2. Water-Soluble Sodium Salt of Betulin-3,28-diphosphate
2.3. Biological Activity of Betulin-3,28-diphosphate In Vitro Experiments
3. Materials and Methods
3.1. Materials
3.2. FTIR Analysis
3.3. NMR Analysis
3.4. Differential Scanning Calorimetry
3.5. Thermogravimetric Analysis
3.6. Powder X-ray Diffraction Analysis
3.7. Synthetic Procedures
3.7.1. Synthesis of Betulin-3,28-diphosphate (BDP, 3β,28-diphosphate-lup-20(29)-ene)
3.7.2. Synthesis of the Sodium Salt of Betulin-3,28-diphosphate
3.8. Biological Activity In Vitro
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are available from the authors. |
Type of BDP | Sample | Melting Point, °С | Peak 1 | Peak 2 | Peak 3 | ||||
---|---|---|---|---|---|---|---|---|---|
Tpeak, °С | Tonset, °С | Tpeak, °С | Exo-Effect ΔH, kJ∙mol−1 | Tonset, °С | Tpeak, °С | Exo-Effect ΔH, kJ∙mol−1 | |||
1 | Readily soluble in ethanol (up to 10%) | 148 | 85.3 ± 0.5 | 151.2 ± 0.5 | 155.9 ± 0.5 | −15.5 ± 0.2 | 183.5 ± 0.5 | 200.8 ± 0.5 | −19.7 ± 0.2 |
2 | After boiling water treatment during 1 h | 157 | 77.0 ± 0.5 | 143.2 ± 0.5 | 161.0 ± 0.5 | −10.0 ± 0.1 | 171.0 ± 0.5 | 185.1 ± 0.5 | −80.4 ± 0.8 |
Synthesis from Na-BDP 2 | 156 | 90.8 ± 0.5 | 137.5 ± 0.5 | 148.5 ± 0.5 | −21.4 ± 0.2 | 164.2 ± 0.5 | 187.3 ± 0.5 | −67.1 ± 0.7 | |
Reprecipitation by acetone | 160 | 94.1 ± 0.5 | 161.3 ± 0.5 | 172.8 ± 0.5 | −23.5 ± 0.2 | 185.9 ± 0.5 | 197.3 ± 0.5 | −70.5 ± 0.7 |
Parameters | % of Control | |
---|---|---|
BDP-1 as Sodium Salt | Mixture of BDP-1 and BDP-2 (2:1) 2 | |
Catalase | 299.0 ± 13.6 | 170.5 ± 3.5 |
SOD | 334.9 ± 2.0 | 165.2 ± 2.5 |
MDAplasma | 98.9 ± 13.0 | 115.07 ± 0.2 |
MDAerythrocyte | 57.0 ± 8.0 | 83.1 ± 3.7 |
LDHdirect | 423.6 ± 7.0 | 271.2 ± 6.5 |
LDHreverse | 236.6 ± 4.0 | 110.0 ± 3.0 |
LPOplasma | 92.8 ± 0.9 | 101.2 ± 0.7 |
LPOerythrocyte | 68.6 ± 0.5 | 96.8 ± 1.4 |
TAS | 117.6 ± 1.9 | 102.7 ± 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. https://doi.org/10.3390/molecules23051175
Melnikova NB, Malygina DS, Klabukova IN, Belov DV, Vasin VA, Petrov PS, Knyazev AV, Markin AV. Betulin-3,28-diphosphate. Physico-Chemical Properties and In Vitro Biological Activity Experiments. Molecules. 2018; 23(5):1175. https://doi.org/10.3390/molecules23051175
Chicago/Turabian StyleMelnikova, Nina B., Darina S. Malygina, Irina N. Klabukova, Denis V. Belov, Viktor A. Vasin, Pavel S. Petrov, Alexander V. Knyazev, and Alexey V. Markin. 2018. "Betulin-3,28-diphosphate. Physico-Chemical Properties and In Vitro Biological Activity Experiments" Molecules 23, no. 5: 1175. https://doi.org/10.3390/molecules23051175