303114-51-4Relevant articles and documents
Complete assignment of 1H and 13C NMR spectra of new pentacyclic triterpene acid benzyl esters
Weis, Robert,Seebacher, Werner
, p. 455 - 457 (2002)
Complete assignments of 1H and 13C NMR chemical shifts for newly synthesized benzyl esters of oleanolic, ursolic and crataegolic acid based on DEPT, HSQC, HMBC, COSY, TOCSY, NOE and ROESY experiments are reported. Copyright
Semi-synthesis and antiproliferative evaluation of PEGylated pentacyclic triterpenes
Medina-O'Donnell, Marta,Rivas, Francisco,Reyes-Zurita, Fernando J.,Martinez, Antonio,Martin-Fonseca, Samuel,Garcia-Granados, Andres,Ferrer-Martín, Rosa M.,Lupia?ez, Jose A.,Parra, Andres
, p. 64 - 78 (2016)
Several PEGylated derivatives of oleanolic and maslinic acids have been semi-synthesized, attaching one acid-PEG reagent to the hydroxyl group/s at C-2 or C-2/C-3 of the A rings of these natural triterpenes, and also to their corresponding C-28 benzyl derivatives. Several monomeric and dimeric PEGylated compounds have also been produced by linking one diamine-PEG reagent to the carboxyl group at C-28 of the same natural triterpenes and also to their corresponding C-2 or C-2/C-3 acetylated derivatives. The cytotoxic effects of 12 triterpenic PEGylated derivatives in three cancer-cell lines (B16F10, HT29, and Hep G2) have been assayed. The best results have been achieved by the PEGylated-amine derivative of oleanolic acid, with IC50 concentrations between 0.22 and 3.78 μM, being between 28- and 963-fold more effective than its natural precursor. The percentages of apoptosis induction have also been determined for the five PEGylated derivatives with the lowest cytotoxicity data. All five compounds showed apoptotic effects on the treated cells, with a total apoptosis rate of 99% in the B16F10 cells, 80% in the Hep G2 cells, and 51% in the HT29 cells. We have also studied the changes in the mitochondrial membrane potential (MMP) to elucidate the possible mechanism involved in the apoptotic responses (intrinsic or extrinsic). Finally, to verify the results found in the cytometry assays, we have used fluorescence microscopy techniques to determine changes in the cell morphology. These PEGylated derivatives of natural triterpenoids, which can induce apoptosis at very low concentrations in different tumour lines, may represent new effective therapeutic drugs against these diseases.
Synthesis and antitumor activity evaluation of oleanolic acid saponins bearing an acetylated L-arabinose moiety
Zhong, Ye,Li, Hui-ning,Zhou, Lin,Su, Hua-sheng,Cheng, Mao-sheng,Liu, Yang
, (2021/04/19)
A series of oleanolic acid derivatives bearing acetyl-substituted L-arabinose moiety has been synthesized and screened in vitro for cytotoxicity against ten cancer cell lines and four normal cell lines. The antiproliferative evaluation indicated that synt
Oleanolic acid and δ - oleanolic acid derivative and medical application thereof (by machine translation)
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Paragraph 0125-0128; 0547-0550, (2021/01/15)
The invention discloses a derivative of a pentacyclic triterpene novel AMPK agonist oleanolic acid and δ - oleanolic acid and a medical application thereof, in particular to a compound shown in formula I or formula II. A pharmaceutically acceptable salt or ester or solvate thereof, which can be used to prepare AMPK agonists with enhanced AMPK phosphorylation level activity and to the preparation of drugs for preventing or treating AMPK mediated diseases. The novel pentacyclic triterpene compound has remarkable AMPK agonist activity, and the activity is remarkably superior to the recognized AMPK agonist AICICAR, and meanwhile, the novel pentacyclic triterpene compound has pharmacokinetic properties such as better oral bioavailability and very good safety. (by machine translation)
