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.
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
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.
-
Huneck,S.
, p. 479 - 482 (1963)
-
-
Agarwal,S.K.,Rastogi,R.P.
, p. 666 - 668 (1974)
-
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.
Electrophilic Triterpenoid Enones: A Comparative Thiol-Trapping and Bioactivity Study
Del Prete, Danilo,Taglialatela-Scafati, Orazio,Minassi, Alberto,Sirignano, Carmina,Cruz, Cristina,Bellido, Maria L.,Mu?oz, Eduardo,Appendino, Giovanni
, p. 2276 - 2283 (2017)
Bardoxolone methyl (1) is the quintessential member of triterpenoid cyanoacrylates, an emerging class of bioactive compounds capable of transient covalent binding to thiols. The mechanistic basis for this unusual "pulsed reactivity" profile and the mode of its biological translation are unknown. To provide clues on these issues, a series of Δ1-dehydrooleanolates bearing an electron-withdrawing group at C-2 (7a-m) were prepared from oleanolic acid (3a) and comparatively investigated in terms of reactivity with thiols and bioactivity against a series of electrophile-sensitive transcription factors (Nrf2, NF-κB, STAT3). The emerging picture suggests that the triterpenoid scaffold sharply decreases the reactivity of the enone system by steric encumbrance and that only strongly electrophilic and sterically undemanding substituents such as a cyanide or a carboxylate group can re-establish Michael reactivity, albeit in a transient way for the cyanide group. In general, a substantial dissection between the thiol-trapping ability and the modulation of biological end-points sensitive to thiol alkylation was observed, highlighting the role of shape complementarity for the activity of triterpenoid thia-Michael acceptors.
Incorporation of a Michael acceptor enhances the antitumor activity of triterpenoic acids
Heller, Lucie,Schwarz, Stefan,Perl, Vincent,K?witsch, Alexander,Siewert, Bianka,Csuk, René
, p. 391 - 399 (2015)
Finding and developing drugs for the treatment of cancer has been challenging scientists for many decades, and using compounds of natural origin represents one of several strategies. Triterpenoic acids are a very promising class of secondary metabolites being able to induce apoptosis while their cytotoxicity is low. Therefore, derivatizations have to be conducted to improve cytotoxicity while retaining their ability to induce programmed cell death. The incorporation of a Michael acceptor into molecules resulted very often in drugs of improved cytotoxicity. Thus, in this study we synthesized and evaluated several Michael acceptor substituted compounds derived from glycyrrhetinic, ursolic, oleanolic and platanic acid. The influence of the presence of such a functional group onto the cytotoxicity was investigated in colorimetric sulforhodamine B assays employing several human cancer cell lines. EC50 values in the single-digit micromolar range were measured. Thus, the incorporation of a Michael acceptor unit into triterpenoic acids enhances the cytotoxicity of these compounds significantly.
COMPOSITIONS COMPRISING ACIDIC EXTRACTS OF MASTIC GUM AND USES THEREOF FOR TREATING OPTIC NEUROPATHY
-
, (2018/03/28)
The invention relates to compositions and formulations comprising isolated acidic fraction of mastic gum and uses thereof for treating optic neuropathy conditions.
