Extraction of betulin from birch bark and study of its physico-chemical and pharmacological properties

Kuznetsova, S. A.; Skvortsova, Galina P.; Маляр, Ю.Н.; Skurydina, E. S.; Veselova, O.F.

doi:10.1134/s1068162014070073

Cited by 38 publications

(40 citation statements)

References 9 publications

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“…The amount of BE in the dry weight varies from 10% to even 45%, and this broad range is the consequence of numerous factors, like tree species and age, weather conditions, regional location etc. (Yogeeswari and Sriram 2005;Kuznetsova et al 2014). BE is also present in the root skin and leaves, although the content is significantly lower when compared to the outer bark (Š iman et al 2016).…”

Section: Betulinmentioning

confidence: 99%

Betulin and betulinic acid: triterpenoids derivatives with a powerful biological potential

et al. 2019

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Betulin, a pentacyclic triterpene and a plant pentacyclic triterpene metabolite, can be found in large quantities in the outer bark of the birches (Betula, Betulaceae). Betulinic acid, obtained by betulin oxidation, is also abundantly present in nature. Both compounds show a wide spectrum of biological and pharmacological properties, such as anti-HIV, anti-inflammatory, and, considered the most important, anti-cancer. Although the specific mechanism of action of betulin against malignant cells is still a subject of detailed research, the activity of betulin acid has been linked to the induction of the intrinsic pathway of apoptosis. As this process occurs with the sparing of non-cancer cells, and the induction of apoptosis can occur under conditions in which standard therapies fail, both substances seem as promising experimental anti-cancer drugs. The aim of this review is to comprehensively summarise the potential of betulin and betulinic acid, both in vitro and in vivo. The discovery, structure, organic synthesis and derivatives forming were shortly described. Also, the potential molecular mechanisms of action and numerous medical applications of betulin and betulinic acid were presented, including previous studies of anti-cancer activity of the compounds, with listed cancer cell types susceptible to therapy.

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Section: Betulinmentioning

confidence: 99%

Betulin and betulinic acid: triterpenoids derivatives with a powerful biological potential

et al. 2019

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“…Betulin was isolated from birch bark (Betula Pendula) using the methods [27]. The materials were meglumine (Merck, TD 13015143333), xymedon (Sigma Aldrich, Moscow, Russia), lithium perchlorate (Sigma Aldrich, Moscow, Russia), phytic acid solution 50 % (w/w) in H2O (Sigma Aldrich, Moscow, Russia), purified water (resistivity ≥18 MΩ•cm, Millipore, Merck, Darmstadt, Germany).…”

Section: Methodsmentioning

confidence: 99%

The Improvement of Betulin-3, 28-Diphosphate Water-Solubility by Complexation With Amines–meglumine and Xymedon

Мельникова

Malygina

Panteleev

et al. 2019

Int J Pharm Pharm Sci

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Objective: To study betulin-3,28-diphosphate (BDP) water solubility improved by forming salt complexes with hydrophilic amino alcohols: meglumine as acidosis corrector and xymedon as the water-soluble antioxidant. Methods: We used 13C-, 31P-NMR, UV-spectroscopy and potentiometric titration to study the BDP-amine salt complexes formation and their solubility using HPLC-analysis. Results: The participation of xymedon in the proton transfer reaction with BDP in aqueous solutions was confirmed by the bathochromic shift of the carbonyl band from 299.1 nm to 304.2 nm, and by a hyperchromic effect (molar extinction ε from 8508 to 10 441 l·mol-1·cm-1) in UV-spectra. BDP complexation with meglumine was estimated by UV-spectral molar ratio method at 256 nm. Molar ratio of BDP-amine complexes (1:4) was proved by 31P-NMR. The chemical shift of phosphorus at C-3 atom of BDP (δ =-0.58 ppm) changed to+3.39 ppm, and at C-28 atom (δ =+0.28 ppm)–to+4.60 ppm. BDP solubility increased 100-600 fold according to HPLC-analysis. Conclusion: BDP interaction with amine in an aqueous solution was shown to proceed via a proton transfer due to relatively weak forces such as London forces, hydrogen bonding, electrostatic and hydrophobic interactions. In general, the formation of BDP salt complexes with amines in solution determines BDP water solubility. Water-soluble BDP enables to develop hydrophilic dosage forms.

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“…The following triterpenes are the most common in the outer bark of the white birch: betulin, lupeol, betulinic acid, oleanolic acid, and erythrodiol ( Figure 1) [3,4]. There are different ways described in the literature to extract and isolate these triterpenes, such as extraction of triterpenoids with organic solvents like n-heptane [4,5] or ethanol [6]. Other methods used include supercritical fluid technology [3], ultrasonic-assisted extraction [7], and sublimation [8].…”

Section: Introductionmentioning

confidence: 99%

“…Triterpenes have antiviral, antibacterial, and antitumoral activities [9,10]. Moreover, a triterpene extract from the outer bark of birch was shown to enhance wound healing ex vivo as well as in vivo There are different ways described in the literature to extract and isolate these triterpenes, such as extraction of triterpenoids with organic solvents like n-heptane [4,5] or ethanol [6]. Other methods used include supercritical fluid technology [3], ultrasonic-assisted extraction [7], and sublimation [8].…”

Section: Introductionmentioning

confidence: 99%

Oleogels with Birch Bark Dry Extract: Extract Saving Formulations through Gelation Enhancing Additives

Ghaffar

Daniels

2020

Pharmaceutics

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Triterpenes from the outer bark of birch have many beneficial biological and pharmacological activities. In particular, its wound healing efficacy is of paramount importance. Apart from that, particles of a birch bark dry extract aggregate into a three dimensional network when they are dispersed in lipids yielding a semi-solid oleogel. However, gel formation requires high amounts of the extract, which then acts at once as the active ingredient and the gelling agent. Infrared spectra of the respective mixtures proved that hydrogen bonds play a crucial role in the formation of the gel network. Dicarboxylic acids had almost no effect on gel strength. Monoalcohols increased the firmness of the oleogel with a decreasing effect from methanol > ethanol > butanol > octanol. All tested terminal diols increased the gel strength whereas vicinal diols affected the gel strength negatively. The effect was highly dependent on their concentration. The different effects of the diols are linked to their structure and polarity. The most pronounced enhancement of gelation was found for 1,6-hexanediol, which reduced the amount of triterpene extract (TE), which is necessary for the formation of an oleogel by a factor of 10.

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Extraction of betulin from birch bark and study of its physico-chemical and pharmacological properties

Cited by 38 publications

References 9 publications

Betulin and betulinic acid: triterpenoids derivatives with a powerful biological potential

Betulin and betulinic acid: triterpenoids derivatives with a powerful biological potential

The Improvement of Betulin-3, 28-Diphosphate Water-Solubility by Complexation With Amines–meglumine and Xymedon

Oleogels with Birch Bark Dry Extract: Extract Saving Formulations through Gelation Enhancing Additives

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