42447-82-5Relevant 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.
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.
Synthesis of Amino Derivates of Ursolic Acid
Jain, S. M.,Atal, C. K.
, p. 427 - 428 (2007/10/02)
Methyl ester of 3β-amino-18β-H-urs-12-en-28-oic acid (VI) has been obtained from methyl ursolate (II) by oxidation with Kiliani reagent (CrO3) to methyl ursonate (IV) followed by treatment of IV with NH2OH/HCl and reduction of the resultant oxime (V) with alkali metal in 1-propanol.Refluxing of acetylursolic acid (III) with thionyl chloride followed by treatment with dry ammonia gas yields the amide (VII) which on LAH reduction affords 3β-acetoxy-18β-H-urs-12-en-28-methyl amine (VIII).Compound III on Curtius rearrangement gives 28-amino-3β-acetoxy-18β-H-urs-12-ene (IX).
