72808-18-5Relevant academic research and scientific papers
Hyaluronidase inhibitory activity of pentacylic triterpenoids from prismatomeris tetrandra (Roxb.) K. schum: Isolation, synthesis and QSAR Study
Abdullah, Nor Hayati,Thomas, Noel Francis,Sivasothy, Yasodha,Lee, Vannajan Sanghiran,Liew, Sook Yee,Noorbatcha, Ibrahim Ali,Awang, Khalijah
, (2016/02/26)
The mammalian hyaluronidase degrades hyaluronic acid by the cleavage of the β-1,4-glycosidic bond furnishing a tetrasaccharide molecule as the main product which is a highly angiogenic and potent inducer of inflammatory cytokines. Ursolic acid 1, isolated from Prismatomeris tetrandra, was identified as having the potential to develop inhibitors of hyaluronidase. A series of ursolic acid analogues were either synthesized via structure modification of ursolic acid 1 or commercially obtained. The evaluation of the inhibitory activity of these compounds on the hyaluronidase enzyme was conducted. Several structural, topological and quantum chemical descriptors for these compounds were calculated using semi empirical quantum chemical methods. A quantitative structure activity relationship study (QSAR) was performed to correlate these descriptors with the hyaluronidase inhibitory activity. The statistical characteristics provided by the best multi linear model (BML) (R2 = 0.9717, R2cv = 0.9506) indicated satisfactory stability and predictive ability of the developed model. The in silico molecular docking study which was used to determine the binding interactions revealed that the ursolic acid analog 22 had a strong affinity towards human hyaluronidase.
Synthesis and antitumor activity evaluation of novel ursolic acid derivatives
Meng, Yan-Qiu,Zhang, Liang-Feng,Liu, Dong-Ying,Liu, Li-Wei,Zhang, Yi,Zhao, Min-Jie
, p. 280 - 288 (2016/04/05)
Eleven novel ursolic acid (UA) derivatives were designed and synthesized with modification at positions of C-2, C-3, and C-28 of UA. Their structures were confirmed by MS, 1H NMR, and elemental analysis. Their in vitro cytotoxicities against various cancer cell lines (HeLa, HepG2, and BGC-823) were evaluated by MTT assay. The results indicated that all compounds could inhibit cell proliferation of HeLa, HepG2, and BGC-823 cells. Among them, compounds I3 and I4 showed more potent cytotoxicity on these three tumor cells than gefitinib (positive control), worthy to be studied further.
Synthesis and cytotoxic activity of ursolic acid derivatives
Thien, Dao Duc,Tam, Nguyen Thanh,Thien, Dinh Gia,Anh, Nguyen Thi Hoang,Van Sung, Tran
, p. 201 - 206 (2013/04/24)
Fourteen ursolic acid derivatives, among them four novel compounds, were synthesized by modification either at the C-3, C-28 or both positions. The cytotoxic activity of the obtained derivatives was evaluated against the four human cancer cell lines KB (human mouth epidermal carcinoma), HepG2 (human hepatocellular carcinoma), MCF7 (human breast carcinoma) and Lu (human lung carcinoma). As the result, compounds 7 and 8 were from two to three times more active than ursolic acid on all four tested cell lines. This is the first report on cytotoxic effects of the synthetized ursolic acid derivatives 4, 8, and 10-15.
The beckmann rearrangement applied to ursolic acid with antimalarial activity in medicinal chemistry studies
Dalla-Vechia, Luciana,Dassonville-Klimpt, Alexandra,Grellier, Philippe,Sonnet, Pascal,Gosmann, Grace,Gnoatto, Simone C.B.
scheme or table, p. 92 - 95 (2012/09/21)
The A ring-expanded derivative of ursolic acid and the corresponding fragmentation product were obtained through the Beckmann rearrangement under optimized reaction conditions. A mechanistic approach was taken in order to explain both the specificity of the rearrangement and the fragmentation of the cycle. The intermediates and the final products of the route were evaluated for antimalarial activity.
The cytotoxic activity of ursolic acid derivatives
Ma, Chao-Mei,Cai, Shao-Qing,Cui, Jing-Rong,Wang, Rui-Qing,Tu, Peng-Fei,Hattori, Masao,Daneshtalab, Mohsen
, p. 582 - 589 (2007/10/03)
Ursolic acid and 2α-hydroxyursolic acid isolated from apple peels were found to show growth inhibitory activity against four tumor cell lines, HL-60, BGC, Bel-7402 and Hela. Structural modifications were performed on the C-3, C-28 and C-11 positions of ursolic acid and the cytotoxicity of the derivatives was evaluated. The SAR revealed that the triterpenes possessing two hydrogen-bond forming groups (an H-donor and a carbonyl group) at positions 3 and 28 exhibit cytotoxic activity. The configuration at C-3 was found to be important for the activity. Introduction of an amino group increased the cytotoxicity greatly. A 3β-amino derivative was 20 times more potent than the parent ursolic acid. The 28-aminoalkyl dimer compounds showed selective cytotoxicity.
