53527-49-4

Usage

Uses

Used in Pharmaceutical Industry:
(4R)-2α,3β,19α-Trihydroxyurs-12-ene-23,28-dioic acid is used as a potential medicinal compound for its unique chemical properties and biological activities. The presence of multiple hydroxyl and carboxylic acid groups allows for interactions with various biological targets, suggesting its potential use in the development of new drugs and therapies.
Used in Research Applications:
In the field of natural products research, (4R)-2α,3β,19α-Trihydroxyurs-12-ene-23,28-dioic acid serves as a valuable subject for studying the structure-activity relationships of triterpenoids and their derivatives. This can lead to a better understanding of their mechanisms of action and the discovery of novel bioactive compounds with potential applications in medicine.

InChI:InChI=1/C30H46O7/c1-16-9-12-30(24(35)36)14-13-26(3)17(21(30)29(16,6)37)7-8-19-25(2)15-18(31)22(32)28(5,23(33)34)20(25)10-11-27(19,26)4/h7,16,18-22,31-32,37H,8-15H2,1-6H3,(H,33,34)(H,35,36)

Upstream product

• 109750-36-9 trachelosperoside A-1 
• 132302-48-8 Coreanogenoic acid 

Downstream Products

• 70868-72-3 Methyl-23-hydroxy-tormentat 

Relevant academic research and scientific papers

A New in vitro Tissue Factor Inhibitory Triterpene from the Fruits of Chaenomeles sinensis

Tissue factor (TF, tissue thromboplastin) accelerates the blood clotting, activating both the intrinsic and the extrinsic pathways to serve as a cofactor. In order to isolate TF inhibitors from the fruits of Chaenomeles sinensis, an activity-guided purification was carried out to yield four triterpenoid compounds. One compound was new and its structure was elucidated as 28-O-β-D-glucopyranosyl-2α,3β-dihydroxyolean-12-ene-24,28-dioic acid (2), named chaenomeloside A by means of spectral analysis and chemical conversion. Other compounds were trachelosperoside A-1 (1), oleanolic acid (3) and ursolic acid (4). Compound 2 and its aglycone 2a, named chaenomelogenin A inhibited by 50 percent the TF activity at concentrations of 0.036 and 0.028 mM/unit of TF, respectively. Compound 1 isolated for the first time from this plant as well as 3 and 4 were inactive.

Constituents of fagaceae (Cupuliferae). XIX: Triterpene saponins and acylated flavonoids from Quercus robur L. var. stenocarpa Beck.

In addition to four known glycosides from leaves of Quercus robur L. var. stenocarpa Beck. a new triterpene saponin has been isolated and identified as 28-β-D-glucopyranosyl ester of the 2α,3β,19α-trihydroxy-olean-12-ene-24,28-dioic acid (1).

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.

A DIMERIC TRITERPENE-GLYCOSIDE FROM RUBUS COREANUS

A dimer of glucosyl esters of A-ring oxygenated 19α-hydroxyursolic acids was isolated from the leaves of Rubus coreanus together with the monomers of the related glucosyl esters.The structure of this compound, named coreanoside F1, was elucidated by chemical and spectroscopic methods.The significance of coreanoside F1 in the identification of the source plants of an oriental traditional medicine "Bog-bun-ja" (= Fu-pen-zi) is discussed.