Betulin, betulonic acid, 3-aminobetulinic acid. Improved extraction and preparative syntheses of derivatives

Kaverin, M. V.; Morozova, P. A.; Snegur, L. V.

doi:10.1007/s11172-022-3651-7

Cited by 7 publications

(2 citation statements)

References 30 publications

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“…Biomedicines 2024, 12, x FOR PEER REVIEW 3 of 37 procedure [20]. Additionally, the advantageous method of BE extraction with the use of aqueous propan-2-ol has been developed, which does not require crystallization [21]. A five-stage purification process has been studied to increase the purity of BE with a yield of about 20% [22].…”

Section: Betulinmentioning

confidence: 99%

“…Such methods include the extraction of BE from an alkaline environment in a microwave field, which allowed an increase in the extraction rate by 15–20 times and significantly accelerated the process in comparison to the standard extraction procedure [ 20 ]. Additionally, the advantageous method of BE extraction with the use of aqueous propan-2-ol has been developed, which does not require crystallization [ 21 ]. A five-stage purification process has been studied to increase the purity of BE with a yield of about 20% [ 22 ].…”

Section: Characteristics Of Betulin and Betulinic Acid And Their Phar...mentioning

confidence: 99%

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Drug Delivery Systems of Betulin and Its Derivatives: An Overview

Jaroszewski,

Jelonek,

Kasperczyk

2024

Biomedicines

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Natural origin products are regarded as promising for the development of new therapeutic therapies with improved effectiveness, biocompatibility, reduced side effects, and low cost of production. Betulin (BE) is very promising due to its wide range of pharmacological activities, including its anticancer, antioxidant, and antimicrobial properties. However, despite advancements in the use of triterpenes for clinical purposes, there are still some obstacles that hinder their full potential, such as their hydrophobicity, low solubility, and poor bioavailability. To address these concerns, new BE derivatives have been synthesized. Moreover, drug delivery systems have emerged as a promising solution to overcome the barriers faced in the clinical application of natural products. The aim of this manuscript is to summarize the recent achievements in the field of delivery systems of BE and its derivatives. This review also presents the BE derivatives mostly considered for medical applications. The electronic databases of scientific publications were searched for the most interesting achievements in the last ten years. Thus far, it is mostly nanoparticles (NPs) that have been considered for the delivery of betulin and its derivatives, including organic NPs (e.g., micelles, conjugates, liposomes, cyclodextrins, protein NPs), inorganic NPs (carbon nanotubes, gold NPs, silver), and complex/hybrid and miscellaneous nanoparticulate systems. However, there are also examples of microparticles, gel-based systems, suspensions, emulsions, and scaffolds, which seem promising for the delivery of BE and its derivatives.

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Section: Betulinmentioning

confidence: 99%

Section: Characteristics Of Betulin and Betulinic Acid And Their Phar...mentioning

confidence: 99%

Drug Delivery Systems of Betulin and Its Derivatives: An Overview

Jaroszewski,

Jelonek,

Kasperczyk

2024

Biomedicines

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New Type of Ferrocene‐Betulonic Acid Hybrids. Bioactivity, Synthesis, Structure, IR and CD versus DFT Calculations

Snegur,

Kaverin,

Borisov

et al. 2024

ChemistrySelect

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Ferrocene‐modified natural compounds are of interest for the development of new pharmaceuticals due to improved bioavailability, increased bioactivity, and also as redox markers or vectors. Betulin is a natural plant‐derived product with a wide range of pharmacological properties. However, it is limited in its bioavailability and efficacy. In order to enhance its pharmacological profile, the ferrocene modification of betulin was used in this study. A hybrid of the betulin core (up to 30 % betulin in birch bark) with a ferrocene moiety combined through a piperazine linker (compound 12) was prepared in good yield from readily available ferrocene carboxylic acid and betulonic acid, a natural betulin derivative, via coupling reactions. Spectroscopic techniques, including 1H and 13C NMR, IR and UV‐vis spectroscopy, as well as circular dichroism (CD), were applied to characterize the physicochemical and chiroptical properties. The cytotoxicity of the synthesized hybrid 12 and its ferrocene precursor 13 on MCF‐7 human cancer cell lines were in vitro evaluated by the MTT assay. The IC50 cytotoxicity index of 12 was found to be 26 μM. The theoretically calculated energies of the HOMO‐LUMO orbitals and electronic characteristics of betulin 10, betulonic acid 11, hybrid 12 and ferrocenyl piperazine 13 were determined by the DFT method with hybrid functionals ωB97XD, LC‐ωPBE and B3LYP‐D3 and pure M06 L functionals, with a 6‐311+G(d), 6‐31G(d) or TZV basis set.

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Synthesis of 2-nicotinylidene triterpenoids: structure, complexation with palladium, and in vitro cytotoxic activity

Denisov,

Eroshenko

2023

Russ Chem Bull

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Betulin, betulonic acid, 3-aminobetulinic acid. Improved extraction and preparative syntheses of derivatives

Abstract: We optimized the process of extraction and purification of betulin from birch bark and modified preparative syntheses of the simplest derivatives of betulin, namely, betulonic acid, betulonic aldehyde, and 3-aminobetulinic acid, as a platform for subsequent modifications.

Cited by 7 publications

References 30 publications

Drug Delivery Systems of Betulin and Its Derivatives: An Overview

Drug Delivery Systems of Betulin and Its Derivatives: An Overview

New Type of Ferrocene‐Betulonic Acid Hybrids. Bioactivity, Synthesis, Structure, IR and CD versus DFT Calculations

Synthesis of 2-nicotinylidene triterpenoids: structure, complexation with palladium, and in vitro cytotoxic activity

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