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. 2023 Aug 8;28(16):5946.
doi: 10.3390/molecules28165946.

Methods of Analysis and Identification of Betulin and Its Derivatives

Altynaray T Takibayeva  1 , Gulistan K Zhumabayeva  2 , Abdigali A Bakibaev  3 , Olga V Demets  1 , Maria V Lyapunova  3 , Elena A Mamaeva  4 , Rakhmetulla Sh Yerkassov  2 , Rymchan Z Kassenov  5 , Marat K Ibrayev  5
Affiliations

Methods of Analysis and Identification of Betulin and Its Derivatives

Altynaray T Takibayeva et al. Molecules. .

Abstract

This scientific work presents practical and theoretical material on the methods of analysis and identification of betulin and its key derivatives. The properties of betulin and its derivatives, which are determined by the structural features of this class of compounds and their tendency to form dimers, polymorphism and isomerization, are considered. This article outlines ways to improve not only the bioavailability but also the solubility of triterpenoids, as well as any hydrophobic drug substances, through chemical transformations by introducing various functional groups, such as carboxyl, hydroxyl, amino, phosphate/phosphonate and carbonyl. The authors of this article summarized the physicochemical characteristics of betulin and its compounds, systematized the literature data on IR and NMR spectroscopy and gave the melting temperatures of key acids and aldehydes based on betulin.

Keywords: betulin; bioavailability; chemical transformation; the solubility of pentacyclic triterpenoids.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
The structural formula of betulin (1) (3β,28-dihydroxy-20(29)-lupen or lup-20(29)-en-3β,28-diol).
Figure 2
Figure 2
The structural formulas of related substances 2–7 when betulin (1) is extracted from birch bark.
Figure 3
Figure 3
The structural formula of allobetulin (8).
Figure 4
Figure 4
The composition of birch extract.
Figure 5
Figure 5
The conformational state of betulin (1). Green arrows show the interaction and mutual arrangement of which atoms and functional groups determine the geometry of the betulin molecule.
Figure 6
Figure 6
The dimeric structure of betulin (1).
Scheme 1
Scheme 1
The basic approaches to the chemical transformation of betulin (1).
Scheme 2
Scheme 2
The reactions of alcohol groups of betulin (1).
Scheme 3
Scheme 3
The reactions of betulin (1) in cycles A and E.
Scheme 4
Scheme 4
The reactions of betulin (1) associated with the transformation of the isopropenyl group.
Figure 7
Figure 7
The structural formulas and possible ways of fragmentation of the studied compounds in the ion source: (a)—betulin, (b)—betulinic acid, (c)—lupeol, (d)—erythrodiol.
Figure 8
Figure 8
The structural formulas of betulin (1), betulin (9) diacetate and allobetulin (8).
Figure 9
Figure 9
Chromatogram of betulin (1) sample (HPLC analysis).
See this image and copyright information in PMC

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References

    1. Cichewicz R.H., Kouzi S.A. Chemistry, biological activity, and chemotherapeutic potential of betulinic acid for the prevention and treatment of cancer and HIV infection. J. Med. Res. Rev. 2004;24:90–114. doi: 10.1002/med.10053. - DOI - PubMed
    1. Alakurtti S., Makela T., Koskimies S., Kauhaluoma J. Pharmacological properties of the ubiquitous natural product botulin. Eur. J. Pharm. Sci. 2006;29:1–13. doi: 10.1016/j.ejps.2006.04.006. - DOI - PubMed
    1. Şoica C.M., Dehelean C.A., Peev C., Aluas M., Zupko I., Kasa P., Alexa E. Physico-chemical comparison study of betulinic acid, betulin and birch bark extract and in vitro investigation of their cytotoxic effects towards skin epidermoid carcinoma (A431), breast carcinoma (MCF7) and cervix adenocarcinoma (HeLa) cell-lines. Nat. Prod. Res. 2012;26:968–974. doi: 10.1080/14786419.2010.545352. - DOI - PubMed
    1. Yogeeswari P., Sriram D. Betulinic acid and its derivatives: A review on their biological properties. Curr. Med. Chem. 2005;12:657–666. doi: 10.2174/0929867053202214. - DOI - PubMed
    1. Melnikova N., Burlova I., Kiseleva T., Klabukova I., Gulenova M., Kislitsin A., Tanaseichuk B. A practical synthesis of betulonic acid using selective oxidation of betulin on aluminium solid support. Molecules. 2012;17:11849–11863. doi: 10.3390/molecules171011849. - DOI - PMC - PubMed

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