1721-58-0Relevant articles and documents
Application of positive mode atmospheric chemical ionisation to distinguish epimeric oleanolic and ursolic acids
Townley, Chloe,Brettell, Rhea C.,Bowen, Richard D.,Gallagher, Richard T.,Martin, William H.C.
, p. 433 - 442 (2015)
A new and more reliable method is reported for distinguishing the equatorial and axial epimers of oleanolic and ursolic acids and related triterpenoids based primarily on the relative abundance of the [M + H]+ and [M + H - H2O]+ signals in their positive mode atmospheric pressure chemical ionisation mass spectra. The rate of elimination of water, which is the principal primary fragmentation of protonated oleanolic and ursolic acids, depends systematically on the stereochemistry of the hydroxyl group in the 3 position. For the b-epimer, in which the 3-hydroxyl substituent is in an equatorial position, [M + H - H2O]+ is the base peak. In contrast, for the a-epimer, where the 3-hydroxyl group is axial, [M + H]+ is the base peak. This trend, which is general for a range of derivatives of oleanolic and ursolic acids, including the corresponding methyl esters, allows epimeric triterpenoids in these series to be securely differentiated. Confrmatory information is available from the collision-induced dissociation of the [M + H - H2O]+ primary fragment ions, which follow different pathways for the species derived from axial and equatorial epimers of oleanolic and ursolic acids. These two pieces of independent spectral information permit the stereochemistry of epimeric oleanolic and ursolic acids (and selected derivatives) to be assigned with confdence without relying either on chromatographic retention times or referring to the spectra or other properties of authentic samples of these triterpenoids.
Synthesis of novel [3,2-b] furan-fused pentacyclic triterpenoids via gold - Catalyzed intramolecular heterocyclization of 2-alkynyl-3-oxotriterpene acids
Gubaidullin, Rinat R.,Khalitova, Rezeda R.,Galimshina, Zulfiya R.,Spivak, Anna Yu
, p. 1888 - 1899 (2018)
A direct and atom-economical synthetic route to new [3,2-b] furan-fused pentacyclic triterpenoids has been developed, using gold-catalyzed 5-exo-dig heterocyclization of accessible 2-alkynyl derivatives of betulonic, ursonic, and oleanonic acids.
Oleanolic acid analogs as NO, TNF-α and IL-1β inhibitors: Synthesis, biological evaluation and docking studies
Bhandari, Pamita,Patel, Neeraj Kumar,Gangwal, Rahul P.,Sangamwar, Abhay T.,Bhutani, Kamlesh Kumar
, p. 4114 - 4119 (2014)
A series of oleanolic acid analogs, characterized by structural modifications at position C-3 and C-28 of oleanane skeleton were synthesized and assessed for antiinflammatory potential towards lipopolysaccharide (LPS) induced nitric oxide (NO) production
Type and position of linkage govern the cytotoxicity of oleanolic acid rhodamine B hybrids
Heise, Niels,Hoenke, Sophie,Simon, Vivienne,Deigner, Hans-Peter,Al-Harrasi, Ahmed,Csuk, René
, (2021)
Oleanolic acid/rhodamine B hybrids exhibit different cytotoxicity depending on the way these two structural elements are linked. While a hybrid holding a piperazinyl spacer at C-28 proved to be cytotoxic in the nano-molar concentration range, hybrids with a direct linkage of the Rho B residue to C-3 of the triterpenoid skeleton are cytotoxic only in the low micro-molar concentration range without any selectivity. This once again underlines the importance of selecting the right spacer and the most appropriate position on the skeleton of the triterpene to achieve the most cytotoxic hybrids possible.
The analgesic and anti-inflammatory effect of new oleanolic acid acyloxyimino derivative
Bednarczyk-Cwynar, Barbara,Zaprutko, Lucjusz,Marciniak, Joanna,Lewandowski, Grzegorz,Szulc, Michal,Kaminska, Ewa,Wachowiak, Natalia,Mikolajczak, Przemyslaw Lukasz
, p. 549 - 555 (2012)
The new derivative of well-known triterpene, oleanolic acid: methyl 3-octanoyloxyiminoolean-12-en-28-oate 5, was synthesized by the action of caprylic acid on methyl oleanolate 3-oxime in the presence of dicyclohexylcarbodiimide in dioxane. The molecular structure of the obtained product 5 was confirmed by spectral methods. The acute toxicity, locomotor activity, and the dose-dependent analgesic activity were studied. In addition, the effect of compound 5 on morphine-induced analgesic activity, the dose-dependent anti-inflammatory activity and the effect of the compound on diclofenac anti-inflammatory activity study were performed. The results proved a low toxicity (LD50 > 2 g/kg) of the tested product 5, which affected neither vertical nor horizontal locomotor activity in the given range of doses. The triterpene 5 also produced centrally mediated (morphine-like) analgesic action; however, only in the highest dose. The synergistic analgesic activity of 5 and morphine in the doses of 30.0 and 300.0 mg/kg was found. Compound 5 expressed the anti-inflammatory action which did not affect the anti-inflammatory activity of diclofenac after their combined administration.
Novel oleanolic vinyl boronates: Synthesis and antitumor activity
Moreira, Vania M.,Salvador, Jorge A.R.,Sim?es, Sérgio,Destro, Federica,Gavioli, Riccardo
, p. 46 - 56 (2013)
A series of novel oleanane-type pentacyclic triterpenoids bearing a boronate ester moiety at C3 have been synthesized by palladium-catalyzed cross-coupling of bis(pinacolato)diboron with vinyl triflates, in the presence of base, and these compounds were fully characterized by 1D and 2D NMR techniques. Evaluation of their antiproliferative effects on a panel of hematological-based and solid tumor cell lines identified three active oleanolic vinyl boronates that inhibited the growth of leukemia (Jurkat, K562), Burkitt's lymphoma (Jijoye), cervix (Hela), colon (SW480), and ovary (SKOV-3) cancer cells without concomitant inhibition of non-tumoral human fibroblasts. Their mechanisms of action were investigated on the leukemia Jurkat cell line. The results show that the incorporation of boron in the oleanolic acid core combined with the presence of amide bonds afforded compounds with desirable biological effects such as apoptosis induction and inhibition of proteasomal activity on tumor cells, which makes them potential templates for further development in the anticancer drug setting.
Oleanolic acid oxime derivatives and their conjugates with aspirin modulate the NF-κB-mediated transcription in HepG2 hepatoma cells
Krajka-Ku?niak, Violetta,Bednarczyk-Cwynar, Barbara,Paluszczak, Jaros?aw,Szaefer, Hanna,Naro?na, Maria,Zaprutko, Lucjusz,Baer-Dubowska, Wanda
, (2019)
The aim of this study was to evaluate the effect of new oleanolic acid oxime (OAO) derivatives and their conjugates with aspirin (ASP) on the expression and activation of NF-κB in human hepatoma HepG2 cells. OAO derivatives showed a stronger cytotoxic effect against HepG2 cells compared with their conjugates with aspirin. Moreover, conjugation of OAO with ASP led to enhanced downregulation of NF-κB expression and activation. Among the hybrids with ASP, compounds: 19, 3-(2-acetoxy)benzoyloxyiminoolean-12-en-28-oic acid morpholide and 13, 3-(2-acetoxy)benzoyloxyiminoolean-12-en-28-oic acid methyl ester, differing, respectively, in morpholide and methyl ester groups at the C-17 position of oleanolic acid (OA) molecule were the most efficient. COX-2 transcript and protein levels were also diminished after treatment with these compounds. The results of this study indicate that the new derivatives of OAO and particularly their conjugates with ASP, downregulate the expression of COX-2 in HepG2 cells by modulating the NF-κB signaling pathway and suggest their potential application in the prevention of liver inflammation and cancer.
Design and synthesis of novel oleanolic acid based chromenes as anti-proliferative and anti-inflammatory agents
Raghuvanshi, Dushyant Singh,Verma, Narsingh,Singh, Shilpi,Luqman, Suaib,Chand Gupta, Amit,Bawankule, Dnyaneshwar U.,Tandon, Sudeep,Nagar, Abhishek,Kumar, Yogesh,Khan, Feroz
, p. 16782 - 16794 (2018)
A practical and novel approach has been developed for the synthesis of oleanolic acid based chromene analogues. Different α,β-unsaturated carbonyl and chromene derivatives of oleanolic acid were synthesized and evaluated for their anticancer activity. Compounds 6e, 6k, 7e and 7g showed significant anticancer activity within the IC50 range of 12.23-39.04 μg mL-1. The promising derivatives 7e and 7g were further analyzed for their effects on the cell cycle and apoptosis in A-549 and MDA-MB-231 cells, and it was depicted that 7e and 7g triggered apoptosis in A-549 and MDA-MB-231 cells and arrested the cell population in the G2/M phase. The anticancer activity of the most active analogue 7g occurred through microtubule destabilization (IC50: ～3.6 μg mL-1), and it was found to be non-toxic against human erythrocytes. The compounds 7e and 7g significantly inhibited the proinflammatory cytokines TNF-α and IL-6.
Synthesis of novel heterocyclic oleanolic acid derivatives with improved antiproliferative activity in solid tumor cells
Leal, Ana S.,Wang, Rui,Salvador, Jorge A. R.,Jing, Yongkui
, p. 1726 - 1738 (2013)
A series of new oleanane imidazole carbamates, N-acylimidazoles or N-alkylimidazoles were synthesized, characterized and evaluated for their antiproliferative activity in AsPC-1 pancreatic cancer cells. Structure-activity relationship analysis revealed that the N-alkylimidazole 27 was the most active compound with apoptosis induction abilities correlated with upregulation of NOXA and downregulation of Bcl-xL. The antiproliferative activity of compound 27 was further tested in more solid tumor cell lines with IC50 values lower than 1 μM.
Beckmann rearrangement of oxime obtained from oleanolic acid. Structure elucidation of the initial oxime
Bednarczyk-Cwynar, Barbara,Zaprutko, Lucjusz,Froelich, Anna
, p. 115 - 121 (2013)
Seven-membered A-lactam and A-nitrile of methyl oleanolate were synthesized from the corresponding oxime. Many reaction setups were tried to find the optimum conditions. The best results (the highest yield of the desired lactam along with total consumption of starting oxime) were obtained in pyridine with phosphoryl chloride as Lewis acid. The main product was obtained with the yield of about 60%. Mechanism of Beckmann rearrangement for the above triterpenic 3-oxime leading to normal and abnormal product (a lactam and a nitrile, respectively) was explained. The structures of both products were determined and fully characterized by spectral data. The stereoisomerism of the initial oxime was determined on the basis of Beckmann rearrangement product structure and X-ray analysis.
