38736-77-5

Usage

Uses

Used in Pharmaceutical Industry:
Epibetulinic acid is used as an anti-HIV agent for its strong activity against the human immunodeficiency virus. Its unique properties enable it to target and inhibit the virus, providing a potential therapeutic option for the treatment of HIV/AIDS.
Used in Drug Development:
Epibetulinic acid is used as a potent and selective TGR5 agonist in drug development. Its ability to activate the TGR5 receptor suggests potential applications in the treatment of various diseases and conditions, such as metabolic disorders and inflammatory processes, by modulating cellular pathways and promoting a beneficial response.

InChI:InChI=1/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h19-24,31H,1,8-17H2,2-7H3,(H,32,33)/t19-,20+,21-,22+,23+,24+,27-,28+,29+,30-/m0/s1

Upstream product

• 1617-70-5 lupenone 
• 4481-62-3 betulonic acid 

Downstream Products

• 2259-06-5 3β-hydroxy-lup-20(29)-en-28-oic acid methyl ester 
• 2259-06-5 3β-hydroxy-lup-20(29)-en-28-oic acid methyl ester 

Relevant academic research and scientific papers

Synthesis and Antiviral Activity of Hydrazides and Substituted Benzalhydrazides of Betulinic Acid and Its Derivatives

New nitrogen-containing derivatives of betulinic and betulonic acids, hydrazides and N′-benzalhydrazides, were synthesized. Their antiviral activities toward viruses of influenza A virus, herpes simplex type I virus, enterovirus ECHO6, and HIV-1 were studied in vitro. Betulinic acid 3-oxime was found to have the highest activity against the influenza virus. Betulonic acid, betulinic acid 4-chlorobenzalhydrazide, betulonic acid 3-oxime benzalhydrazide, and betulinic acid hydrazide inhibited the replication of herpes simplex type I virus. Betulinic acid hydrazide also showed antiviral activity toward HIV-1. All the derivatives of betulinic acid under study displayed a low antiviral activity toward enterovirus ECHO6.

Lupane-triterpenoids from stem bark of Dillenia indica

A new lupane-triterpene acid ester, dillenic acid 1 along with four known compounds, betulinic acid 2, 3-epi-betulinic acid 3, 3-epi-dihydrobetulinic acid 4 and 3α-hydroxy-lup-20(29)-en-23,28-dioic acid 5 have been isolated from the stem bark of Dillenia indica Linn (Dilleniaceae). Based on spectroscopic and chemical data, the structure of the new compound 1 was determined as 3α-(2-hydroxyhexanoyloxy)-lup-20(29)-en-28-oic acid. Known compounds 3-5 has been reported for the first time from this plant.

Epimerization of Hydroxyl Group in Lupan Series Triterpenoids

Two methods of obtaining 3α-betulinic acid and related compounds from their 3β-epimers were studied: the reaction of bimolecular substitution and the stereoselective reduction of 3-ketoderivatives. The substitution of acyloxy by formyloxy group in 3-O-tosyllupeol or of the belulin hydroxyl by benzoyloxy group resulted only in Δ2, 3-elimination products, with none of the expected products of bimolecular substitution being found. The catalytic hydrogenation of betulonic acid over Raney nickel resulted only in reduction of the isopropenyl double bond, whereas the use of 5% Ru/C gave a 60:40 mixture of epimers of dihydrobetulinic acid. Practically the same mixture of betulinic acid epimers was obtained when reducing betulonic acid with L-Selectride. The cytotoxic activity of 3α-betulinic acid increased toward the Bro melanoma cells and decreased toward the MS melanoma cells.

Synthesis of betulinic acid derivatives with activity against human melanoma

Betulinic acid has been modified at C-3, C-20, and C-28 positions and the toxicity of the derivatives has been evaluated against cultured human melanoma (MEL-2) and human epidermoid carcinoma of the mouth (KB) cell lines. This preliminary investigation demonstrates that simple modifications of the parent structure of betulinic acid can produce potentially important derivatives, which may be developed as antitumor drugs.

The synthesis of betulinic acid from betulin and its solubilization with liposomes

A method for betulinic acid synthesis from betulin was developed. Betulin was oxidized with chromium oxide (VI) into betulonic acid, which was reduced with sodium borohydride to yield a mixture of 3-hydroxy epimers containing 85% of the natural β-epimer. Studying changes in light scattering by dispersions of liposomes with different contents of betulinic acid revealed that up to 10 mol % of this compound may be entrapped in liposomes. The dependence of the efficiency of the betulinic acid entrapment on liposome composition was studied. The presence of polyvinylpyrrolidone or Proxanol increased the resistance of betulinic acid-containing liposomes to aggregation. These polymers solubilized betulinic acid with the same efficiency as liposomes.