13850-16-3

Usage

Uses

Used in Anticancer Applications:
2α,19α-Dihydroxyursolic acid is used as an anticancer agent for its inhibitory effect on carcinogenesis. It may modulate various oncological signaling pathways, exerting inhibitory effects on tumor growth and progression. Additionally, it has the potential to demonstrate synergistic anticancer effects when combined with conventional chemotherapeutic drugs, enhancing chemo-sensitivity and efficacy in resistant cases.
Used in Hepatoprotective Applications:
2α,19α-Dihydroxyursolic acid is used as a hepatoprotective agent for the prevention of acetaminophen (APAP)-induced liver injury. It achieves this by inhibiting oxidative stress and inflammation, which are key factors in liver damage caused by APAP overdose or other hepatotoxic agents.
Used in Pharmaceutical Industry:
2α,19α-Dihydroxyursolic acid is used as a pharmaceutical candidate due to its potential therapeutic properties. Its unique chemical structure and biological activities make it a promising compound for the development of new drugs targeting various diseases, including cancer and liver disorders.
Used in Drug Delivery Systems:
Similar to gallotannin, 2α,19α-Dihydroxyursolic acid may also benefit from novel drug delivery systems to enhance its applications and efficacy against disease targets. Various organic and metallic nanoparticles could be employed as carriers for 2α,19α-Dihydroxyursolic acid delivery, aiming to improve its delivery, bioavailability, and therapeutic outcomes.

InChI:InChI=1/C30H48O5/c1-17-10-13-30(24(33)34)15-14-27(5)18(22(30)29(17,7)35)8-9-21-26(4)16-19(31)23(32)25(2,3)20(26)11-12-28(21,27)6/h8,17,19-23,31-32,35H,9-16H2,1-7H3,(H,33,34)/t17-,19-,20+,21-,22-,23+,26+,27-,28-,29-,30+/m1/s1

Upstream product

• 121064-78-6 3-O-trans-p-coumaroyltormentic acid 
• 95298-47-8 2α,3α,19α-trihydroxyurs-12-en-28-oic acid 28-β-D-glucopyranosyl ester 
• 52936-88-6 2α,3α-diacetoxy-19α-hydroxyurs-12-en-28-oic acid 
• 1309589-79-4 2α,19α-dihydroxy-5α,9α-urs-12-en-3-one-28-oic acid-28-O-β-D-glucopyranosyl ester 

Downstream Products

• 13850-15-2 methyl 2α,3β,19-trihydroxyurs-12-en-28-oate 
• 13849-91-7 polnolic acid 
• 63478-78-4 methyl 2α,3α-diacetoxy-19α-hydroxyurs-12-en-28-oate 
• 52936-89-7 methyl 2α,3α,19-trihydroxyurs-12-en-28-oate 
• 1412898-52-2 (2R,19R)-methyl 2-acetyloxy-19-hydroxy-3-oxours-12-en-28-carboxylate 
• 52936-88-6 2α,3α-diacetoxy-19α-hydroxyurs-12-en-28-oic acid 
• 97094-23-0 (2R,3R,19R)-3-acetyloxy-2,19-dihydroxyurs-12-en-28-carboxylic acid 
• 97094-22-9 (2R,3R,19R)-2-acetyloxy-3,19-dihydroxyurs-12-en-28-carboxylic acid 
• 14539-80-1 Diacetyl-tormentsaeure-methylester 
• 13850-14-1 (2R,3R,19R)-2,3-bis(acetyloxy)-19-hydroxyurs-12-en-28-carboxylic acid 

Relevant academic research and scientific papers

Bioactive Triterpenoids from the Twigs of Chaenomeles sinensis

Chaenomeles sinensis has been consumed traditionally for the treatment of throat diseases, diarrhea, inflammatory diseases, and dry beriberi. Repeated chromatography of the CHCl3-soluble fraction from the 80% MeOH extract of C. sinensis twigs led to the isolation of three new triterpenoids, sinenic acid A (1), 3β-O-cis-feruloyl-2α,19α-dihydroxyurs-12-en-28-oic acid (2), and 3β-O-cis-caffeoylbetulin (3), together with 20 analogues. The chemical structures of 1-3 were determined using diverse NMR techniques and HRMS data analysis, chemical methods, and computational approaches supported by advanced statistics (CP3). All the purified compounds were evaluated not only for their cytotoxicity against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15) but for their potential neuroprotective effects through induction of nerve growth factor in C6 glioma cells. Their anti-inflammatory effects were also assessed by measuring nitric oxide levels in lipopolysaccharide-insulted murine microglia BV2 cells.

Ursane saponins from the stems of Firmiana simplex and their cytotoxic activity

Three new ursane triterpene saponins, together with twelve known ursane triterpenes were isolated from the stems of Firmiana simplex. The structures of the saponines were elucidated on the basis of spectroscopic and chemical methods. The cytotoxic activity of all compounds was evaluated in vitro against lung adenocarcinoma (A549), ovarian cancer (SK-OV-3), skin melanoma (SK-MEL-2), and colon cancer (HCT-15) human cell lines, using a sulforhodamine (SRB) assay. 23-Hydroxyursolic acid showed cytotoxicity against the tested cell lines with IC50 values ranging from 11.96 to 14.11 μM.

Hepatoprotective triterpenes from traditional Tibetan medicine Potentilla anserina

A methanol extract from the tuberous roots of Potentilla anserina (Rosaceae) exhibited hepatoprotective effects against d-galactosamine (d-GalN)/lipopolysaccharide-induced liver injuries in mice. Six triterpene 28-O-monoglucopyranosyl esters, potentillanosides A-F, were isolated from the extract along with 32 known compounds, including 15 triterpenes. The structures of potentillanosides A-F were determined on the basis of spectroscopic properties and chemical evidence. Four ursane-type triterpene 28-O-monoglycosyl esters, potentillanoside A (IC50 = 46.7 μM), 28-O-β-d- glucopyranosyl pomolic acid (IC50 = 9.5 μM), rosamutin (IC 50 = 35.5 μM), and kaji-ichigoside F1 (IC50 = 14.1 μM), inhibited d-GalN-induced cytotoxicity in primary cultured mouse hepatocytes. Among these four triterpenes, potentillanoside A, rosamutin, and kaji-ichigoside F1 exhibited in vivo hepatoprotective effects at doses of 50-100 mg/kg, p.o. The mode of action was ascribable to the reduction in cytotoxicity caused by d-GalN.

11β-Hydroxysteroid dehydrogenase 1 inhibiting constituents from Eriobotrya japonica revealed by bioactivity-guided isolation and computational approaches

The inhibition of 11β-hydroxysteroid dehydrogenase 1 (11β-HSD1), which catalyzes the conversion of inactive 11-ketoglucocorticoids to active 11β-hydroxyglucocorticoids, emerged as promising strategy to treat symptoms of the metabolic syndrome, including obesity and type 2 diabetes. In this study the leaves of the anti-diabetic medicinal plant loquat (Eriobotrya japonica) were phytochemically investigated following hints from a pharmacophore-based virtual screening and a bioactivity-guided approach. Determination of the 11β-HSD1 and 11β-HSD2 inhibitory activities in cell lysates revealed triterpenes from the ursane type as selective, low micro-molar inhibitors of 11β-HSD1, that is, corosolic acid (1), 3-epicorosolic acid methyl ester (4), 2-α hydroxy-3-oxo urs-12-en-28-oic acid (6), tormentic acid methyl ester (8), and ursolic acid (9). Importantly, a mixture of loquat constituents with moderate activities displayed a pronounced additive effect. By means of molecular modeling studies and the identification of the 11β-HSD1-inhibiting 11-keto-ursolic acid (17) and 3-acetyl-11-keto-ursolic acid (18) a structure-activity relationship was deduced for this group of pentacyclic triterpenes. The mechanism of action elucidated in the present work together with the previously determined pharmacological activities provides these natural products with an astonishing multi-targeted anti-diabetic profile.

Retrovirus protease inhibitors

A compound composition and method of treating a retrovirus infection are disclosed. In particular, isolated triterpenes have been shown to have significant inhibitory activity against HIV-1.

An E-ring γ-lactone pentacyclic triterpene from Myrianthus serratus

A novel γ-lactone triterpenoid has been isolated from the methylated ethyl acetate extract of the trunk wood of Myrianthus serratus, as well as friedelin and four known pentacyclic triterpenoid acids, all as their methyl esters. Their structures were elucidated by 2D NMR experiments.

β-GLUCOSYL ESTERS OF 19α-HYDROXYURSOLIC ACID DERIVATIVES IN LEAVES OF RUBUS SPECIES

Key Word Index-Rubus microphyllus; R. koehneanus; R. trifidus; R. medius; Rosaceae; triterpene glucosyl esters; 19α-hydroxyursolic acid derivatives. β-Glucosyl esters of A-ring oxygenated 19α-hydroxyursolic acids were isolated from the leaves of Rubus microphyllus, R. koehneanus, R. trifidus and R. medius.Comparisons of the glycoside fractions of the leaves of 39 Rubus species were conducted, indicating the chemotaxonomic significance of this type of glucosyl ester in this genus.