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.
Rapid Self-Healing and Thixotropic Organogelation of Amphiphilic Oleanolic Acid-Spermine Conjugates
?zdemir, Zulal,?aman, David,Bertula, Kia,Lahtinen, Manu,Bednárová, Lucie,Pazderková, Markéta,Rárová, Lucie,Nonappa,Wimmer, Zdeněk
, p. 2693 - 2706 (2021/03/15)
Natural and abundant plant triterpenoids are attractive starting materials for the synthesis of conformationally rigid and chiral building blocks for functional soft materials. Here, we report the rational design of three oleanolic acid-triazole-spermine
Oleanolic acid derivative with conjugated diene structure C ring and preparation method and application thereof
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Paragraph 0087-0091, (2020/07/21)
The invention belongs to the field of medicinal chemistry, and particularly relates to an oleanolic acid derivative with a conjugated diene structure C ring and a preparation method and application thereof. In particular, the invention also provides a pharmaceutical composition comprising an effective amount of the derivative or pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier; moreover, the derivative or the pharmaceutically acceptable salt thereof can be used for treating inflammation-related diseases and has antitumor activity, and the safety of the compound is improved or equivalent.
