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
Oleanolic acid-amino acids derivatives: Design, synthesis, and hepatoprotective evaluation in vitro and in vivo
Chu, Fuhao,Zhang, Wenxi,Guo, Wenbo,Wang, Zhaoyi,Yang, Yuqin,Zhang, Xinyu,Fang, Kang,Yan, Mengmeng,Wang, Penglong,Lei, Haimin
, (2018)
Activated hepatic stellate cells (HSCs) are the main extracellular matrix (ECM)-producing cells in the injured liver and the key mediators of liver fibrosis; they also promote the progression of hepatocellular carcinoma (HCC). In the acidic extracellular
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.
Pentacyclic triterpenoid TGR5 receptor stimulant, preparation method and application thereof
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Paragraph 0123; 0329-0331, (2021/04/26)
The invention discloses a pentacyclic triterpenoid TGR5 receptor stimulant, a preparation method and application of the pentacyclic triterpenoid TGR5 receptor stimulant. The structure of the pentacyclic triterpenoid TGR5 receptor stimulant is as shown in a formula I, and the definition of each substituent is as shown in the specification and claims. According to the pentacyclic triterpenoid compound, the solubility is increased, the permeability is improved, the TGR5 receptor agonist activity is remarkably improved, Caco-2 monolayer cells can be penetrated, and the in-vivo drug effect exertion of the compound after oral administration is guaranteed. The TGR5 receptor stimulant is expected to be further developed into a medicine for treating metabolic diseases represented by diabetes.
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
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 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.
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)
Oleanolic acid C-3-site sugar conjugate, preparation method and anti-influenza virus application thereof
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Paragraph 0035-0036; 0041, (2020/12/05)
The invention provides an oleanolic acid-C-3-site sugar conjugate with a structure shown as a formula (I) or pharmaceutically acceptable salt thereof and a preparation method thereof. The oleanolic acid-C3-site sugar conjugate has an obvious inhibiting effect on influenza viruses and can be used for preparing a medicine for preventing or treating influenza and a drug for preventing or inhibiting the entry of influenza viruses into cells.
Nematicidal activity of oleanolic acid derivatives on Meloidogyne incognita
Ayub, Anjum,Bano, Zarina,Begum, Sabira,Fayyaz, Shahina,Hassan, Nabila,Iqbal, Erum,Kiran, Zareena,Sara, Sara,Siddiqui, Bina S.
, p. 1 - 7 (2020/07/28)
In this study, oleanolic acid and its derivatives were studied for their invivo nematicidal activity against root-knot nematode (RKN) Meloidogyne incognita. A series of C-28-oleanolates including five new (5, 7–10) and seven known (1–4, 6, 11, 12) compounds were synthesised and their nematicidal activity was determined and compared with the standard nematicide furadan for the first time. The structures of the compounds were elucidated through 1H NMR, 13C NMR and EIMS. Compounds 4, 5, 7, 8 and 10 showed ～ 90percent inhibition of RKN at 0.125percent concentration after 72 h showing their potential use in nematicidal control.
