NEW METHODS OF PREPARATION OF ALLOBETULIN 3-O-FORMATE FROM BIRCH BARK AND STUDING ITS INFLUENCE ON BLOOD/PLAZMA COAGULATION

UDC 547.597:547.918

  • Evgeniya Sergeevna Skurydina Institute of Chemistry and Chemical Technology SB RAS Email: zenav@mail.ru
  • Svetlana Alekseevna Kuznetsova Institute of Chemistry and Chemical Technology SB RAS Email: kuznetssvetl@yandex.ru
  • Natalya Nikolaevna Drozd National Medical Research Center of Hematology Email: nndrozd@mail.ru
  • Boris Nikolaevich Kuznetsov Institute of Chemistry and Chemical Technology SB RAS, Federal Research Center KSC SB RAS Email: bnk@icct.ru
DOI_disc_logo https://doi.org/10.14258/jcprm.20250417353
Keywords: birch bark, betulin, allobetulin, 3-0-formate allobetulin, formic acid, blood/plasma coagulation

Abstract

The purpose of this work was to develop a new one-step method for the synthesis of allobetulin 3-O-formate from birch bark, select optimal synthesis conditions and to studing its influence on blood/plasma coagulation. A new one-step method has been proposed for the synthesis of allobetulin 3-O-formate from birch bark Betula Pendula Roth., based on combining the extraction of betulin, its isomerization into allobetulin in the presence of a catalyst - orthophosphoric acid, and the esterification of allobetulin with formic acid. The influence of the duration of the process of treating birch bark with formic acid and the H3PO4 content on the yield of allobetulin 3-O-formate was established. The highest yield of crude allobetulin 3-O-formate (37% by weight of a.d.b.) is achieved at a process duration of 12 hours in the presence of 10% H3PO4, as well as with a duration of 16 hours in the presence of 8% H3PO4. The yield of recrystallized from ethanol allobetulin 3-O-formate is about 30% by weight of the a.d.b. The composition of the obtained samples of recrystallized allobetulin 3-O-formate was determined by elemental analysis, and its structure was confirmed by IR and NMR spectroscopy.

In vitro experiments conducted using human donor blood showed that allobetulin 3-O-formate exhibits pronounced procoagulant properties and does not have a significant effect on the erythrocyte membrane. Allobetulin 3-O-formate can be used to create biomaterials with specified properties in relation to blood coagulation.

Downloads

Download data is not yet available.

Author Biographies

Evgeniya Sergeevna Skurydina, Institute of Chemistry and Chemical Technology SB RAS

Lead Engineer

Svetlana Alekseevna Kuznetsova, Institute of Chemistry and Chemical Technology SB RAS

Doctor of Chemical Sciences, Leading Researcher

Natalya Nikolaevna Drozd, National Medical Research Center of Hematology

Doctor of Biological Sciences, Leading Researcher

Boris Nikolaevich Kuznetsov, Institute of Chemistry and Chemical Technology SB RAS, Federal Research Center KSC SB RAS

Doctor of Chemical Sciences, Professor, Head of Research

References

Räsänen R.M., Hieta J.P., Immanen J., Nieminen K., Haavikko R., Yli-Kauhaluoma J., Kauppila T.J. Analytical and bioanalytical chemistry, 2019, vol. 411, pp. 7573–7583. https://doi.org/10.1007/s00216-019-02171-9.

Hemingway R.W. Organic chemicals from biomass. CRC Press, 2018, pp. 189–248.

Kuznetsov B.N., Levdanskiy V.A., Kuznetsova S.A. Khimicheskiye produkty iz drevesnoy kory. Monografiya. [Chem-ical products from tree bark. Monograph]. Krasnoyarsk, 2012, 260 p. (in Russ.).

Takibayeva A.T., Zhumabayeva G.K., Bakibaev A.A., Demets O.V., Lyapunova M.V., Mamaeva E.A., Yerkass-ov R.Sh., Kassenov R.Z., Ibrayev M.K. Molecules, 2023, vol. 28, no. 16, 5946. https://doi.org/10.3390/molecules28165946.

Kuznetsova S.A., Skvortsova G.P., Maliar I.N., Skurydina E.S., Veselova O.F. Russian Journal of Bioorganic Chem-istry, 2014, vol. 40, pp. 742–747. https://doi.org/10.1134/S1068162014070073.

Adepoju F.O., Duru K.C., Li E., Kovaleva E.G., Tsurkan M.V. Biomolecules, 2023, vol. 13, no. 7, 1105. https://doi.org/10.3390/biom13071105.

Ren L., Niu S., Sun Y., Liang Y., Zhao J., Zhang T., Zhang J. Food and Chemical Toxicology, 2021, vol. 157, 112539. https://doi.org/10.1016/j.fct.2021.112539.

Madej M., Gola J., Chrobak E. Pharmaceutics, 2023, vol. 15, no. 12, 2768. https://doi.org/10.3390/pharmaceutics15122768.

Bębenek E., Chrobak E., Piechowska A., Głuszek S., Boryczka S. Medical Studies/Studia Medyczne, 2020, vol. 36, no. 4, pp. 298–302. https://doi.org/10.5114/ms.2020.102324.

Vorob'yeva O.A., Malygina D.S., Grubova Ye.V., Mel'nikova N.B. Khimiya rastitel'nogo syr'ya, 2019, no. 4, pp. 407–430. https://doi.org/10.14258/jcprm.2019045419. (in Russ.).

Amiri S., Dastghaib S., Ahmadi M., Mehrbod P., Khadem F., Behrooj H., Aghanoori M.-R., Machaj F., Ghamsari M., Rosik J., Hudecki A., Askami A., Hasemi M., Los M.J., Makkaram P, Madrakian T., Ghavami S. Biotechnology ad-vances, 2020, vol. 38, 107409. https://doi.org/10.1016/j.biotechadv.2019.06.008.

Drąg-Zalesińska M., Borska S. World Scientific News, 2019, vol. 127, no. 3, pp. 123–138.

Chrobak E., Świtalska M., Wietrzyk J., Bębenek E. Applied Sciences, 2024, vol. 14(21), 9970. https://doi.org/10.3390/app14219970.

Pinzaru I., Trandafirescu C., Szabadai Z., Mioc M., Ledeti I., Coricovac D., Ciurlea S., Ghiulai R.M., Crainiceanu Z., Simu G. Rev. Chim., 2014, vol. 65, pp. 848–851.

Pęcak P., Orzechowska B., Chrobak E., Boryczka S. European Journal of Medicinal Chemistry, 2021, vol. 225, 113738. https://doi.org/10.1016/j.ejmech.2021.113738.

Kuznetsova S.A., Kuznetsov B.N., Skvortsova G.P., Skurydina Ye.S., Kalacheva G.S. Zhurnal SFU. Khimiya, 2010, vol. 3 (2), pp. 174–182. (in Russ.).

Kuznetsova S.A., Skvortsova G.P., Skurydina Ye.S., Malyar Yu.N., Khanchich O.A. Zhurnal SFU. Khimiya, 2011, vol. 4 (3), pp. 248–256. (in Russ.).

Salah A., Imene B., Abdigali B. Khimiya rastitel'nogo syr'ya, 2019, no. 1, pp. 113–117. https://doi.org/10.14258/jcprm.2019014682.

Arrous S., Boudebouz I., Parunov I., Plotnikov E., Voronova O. Chemistry of Natural Compounds, 2019, vol. 55, pp. 1094–1097. https://doi.org/10.1007/s10600-019-02902-5.

Skurydina Ye.S., Vasil'yeva N.Yu., Kuznetsova S.A., Titova N.M., Kuznetsov B.N. Khimiya rastitel'nogo syr'ya, 2023, no. 3, pp. 243–252. https://doi.org/10.14258/jcprm.20230313179. (in Russ.).

Gulliani G.L., Hyun B.H., Litten M.B. Am. J. Clin. Pathol., 1976, vol. 65, no. 3, pp. 390–396.

Dash B.C., Réthoré G., Monaghan M., Fitzgerald K., Gallagher W., Pandit A. Biomaterials, 2010, vol. 31, no. 32, pp. 8188–8197. https://doi.org/10.1016/j.biomaterials.2010.07.067.

Published
2025-12-12
How to Cite
1. Skurydina E. S., Kuznetsova S. A., Drozd N. N., Kuznetsov B. N. NEW METHODS OF PREPARATION OF ALLOBETULIN 3-O-FORMATE FROM BIRCH BARK AND STUDING ITS INFLUENCE ON BLOOD/PLAZMA COAGULATION // Chemistry of plant raw material, 2025. № 4. P. 327-334. URL: https://journal.asu.ru/cw/article/view/17353.
Issue
No 4 (2025)
Section
Low-molecular weight compounds

Copyright (c) 2025 Chemistry of plant raw material

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.

The authors, which are published in this journal, agree to the following conditions:

1. Authors retain the copyright to the work and transfer to the journal the right of the first publication along with the work, at the same time licensing it under the terms of the Creative Commons Attribution License, which allows others to distribute this work with the obligatory indication of the authorship of this work and a link to the original publication in this journal .

2. The authors retain the right to enter into separate, additional contractual agreements for the non-exclusive distribution of the version of the work published by this journal (for example, to place it in the university depository or to publish it in a book), with reference to the original publication in this journal.

3. Authors are allowed to post their work on the Internet (for example, in a university repository or on their personal website) before and during the review process of this journal, as this may lead to a productive discussion, as well as more links to this published work.

Crossref
Scopus
Google Scholar
Europe PMC