Preparation of Betulinic Acids from Betulin Extract. Antiviral and Antiulcer Activity of Some Related Terpenoids.

Флехтер, О. Б.; Nigmatullina, L. R.; Балтина, Л. А.; Karachurina, L. T.; Галин, Ф. З.; Zarudii, F. S.; Толстиков, Г. А.; Бореко, Е. И.; Pavlova, N. I.; Николаева, С. Н.; al., et

doi:10.1002/chin.200304177

Cited by 8 publications

(14 citation statements)

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“…The antiviral activity of the newly synthesized 2,3-secotriterpene derivatives against VSV was examined in porcine embryo kidney (PEK) cells treated with different concentrations of the test compounds for 1 h at 37 C followed by VSV infection. Betulinic acid (95%) synthesized according to [24] was used as a positive control. Cleanness of betulinic acid was confirmed after methylation [25] by using gas chromatographyemass spectroscopy.…”

Section: Biologymentioning

confidence: 99%

Synthesis, transformation and biological evaluation of 2,3-secotriterpene acetylhydrazones and their derivatives

Гришко

Толмачева

Galaiko

et al. 2013

European Journal of Medicinal Chemistry

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Section: Biologymentioning

confidence: 99%

Synthesis, transformation and biological evaluation of 2,3-secotriterpene acetylhydrazones and their derivatives

Гришко

Толмачева

Galaiko

et al. 2013

European Journal of Medicinal Chemistry

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“…1A) that exists widely in food, medicinal herbs, and plants, especially birch bark [9]. As an oxidation product of betulin (see Fig.…”

Section: Introductionmentioning

confidence: 99%

Betulinic acid prevents alcohol-induced liver damage by improving the antioxidant system in mice

Xia

et al. 2014

J Vet Sci

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Betulinic acid (BA), a pentacyclic lupane-type triterpene, has a wide range of bioactivities. The main objective of this work was to evaluate the hepatoprotective activity of BA and the potential mechanism underlying the ability of this compound to prevent liver damage induced by alcohol in vivo. Mice were given oral doses of BA (0.25, 0.5, and 1.0 mg/kg) daily for 14 days, and induced liver injury by feeding 50% alcohol orally at the dosage of 10 ml/kg after 1 h last administration of BA. BA pretreatment significantly reduced the serum levels of alanine transaminase, aspartate transaminase, total cholesterol, and triacylglycerides in a dose-dependent manner in the mice administered alcohol. Hepatic levels of glutathione, superoxide dismutase, glutathione peroxidase, and catalase were remarkably increased, while malondialdehyde contents and microvesicular steatosis in the liver were decreased by BA in a dose-dependent manner after alcohol-induced liver injury. These findings suggest that the mechanism underlying the hepatoprotective effects of BA might be due to increased antioxidant capacity, mainly through improvement of the tissue redox system, maintenance of the antioxidant system, and decreased lipid peroxidation in the liver.

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“…Substances were detected by 10% H 2 SO 4 with subsequent heating to 100–120 °C for 2–3 min. Betulonic 1 and 3β,28-diacetoxy-(20 R )-lupane-29-oic 3 acids were synthesized accordingly [ 25 , 69 ].…”

Section: Methodsmentioning

confidence: 99%

Evaluation of Cytotoxicity and α-Glucosidase Inhibitory Activity of Amide and Polyamino-Derivatives of Lupane Triterpenoids

et al. 2020

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A series of two new and twenty earlier synthesized branched extra-amino-triterpenoids obtained by the direct coupling of betulinic/betulonic acids with polymethylenpolyamines, or by the cyanoethylation of lupane type alcohols, oximes, amines, and amides with the following reduction were evaluated for cytotoxicity toward the NCI-60 cancer cell line panel, α-glucosidase inhibitory, and antimicrobial activities. Lupane carboxamides, conjugates with diaminopropane, triethylenetetramine, and branched C3-cyanoethylated polyamine methyl betulonate showed high cytotoxic activity against most of the tested cancer cell lines with GI50 that ranged from 1.09 to 54.40 µM. Betulonic acid C28-conjugate with triethylenetetramine and C3,C28-bis-aminopropoxy-betulin were found to be potent micromolar inhibitors of yeast α-glucosidase and to simultaneously inhibit the endosomal reticulum α-glucosidase, rendering them as potentially capable to suppress tumor invasiveness and neovascularization, in addition to the direct cytotoxicity. Plausible mechanisms of cytotoxic action and underlying disrupted molecular pathways were elucidated with CellMinner pattern analysis and Gene Ontology enrichment analysis, according to which the lead compounds exert multi-target antiproliferative activity associated with oxidative stress induction and chromatin structure alteration. The betulonic acid diethylentriamine conjugate showed partial activity against methicillin-resistant S. aureus and the fungi C. neoformans. These results show that triterpenic polyamines, being analogs of steroidal squalamine and trodusquemine, are important substances for the search of new drugs with anticancer, antidiabetic, and antimicrobial activities.

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Preparation of Betulinic Acids from Betulin Extract. Antiviral and Antiulcer Activity of Some Related Terpenoids.

Cited by 8 publications

References 0 publications

Synthesis, transformation and biological evaluation of 2,3-secotriterpene acetylhydrazones and their derivatives

Synthesis, transformation and biological evaluation of 2,3-secotriterpene acetylhydrazones and their derivatives

Betulinic acid prevents alcohol-induced liver damage by improving the antioxidant system in mice

Evaluation of Cytotoxicity and α-Glucosidase Inhibitory Activity of Amide and Polyamino-Derivatives of Lupane Triterpenoids

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