6089-92-5

Usage

Uses

Used in Pharmaceutical Industry:
(2α,3β)2,3-Bis(acetyloxy)-olean12-en-28-oic acid is used as a pharmaceutical compound for its potential anti-inflammatory, anti-cancer, and hepatoprotective effects. The acetylated form of oleanolic acid may have improved solubility and bioactivity, making it a promising candidate for the development of new drugs and therapies.
Used in Drug Delivery Systems:
(2α,3β)2,3-Bis(acetyloxy)-olean12-en-28-oic acid can be used in drug delivery systems to improve the bioavailability and therapeutic outcomes of oleanolic acid and its derivatives. The acetylated form may enhance the solubility and stability of the compound, allowing for more effective delivery to target tissues and cells.

Upstream product

• 4373-41-5 maslinic acid 
• 108-24-7 acetic anhydride 
• 106894-29-5 3-acetylmaslinic acid (TARB-2) 
• 75-36-5 acetyl chloride 
• 4373-41-5 2α,3β-dihydroxyolean-12-en-28-oic acid 
• 1724-16-9 Methyl maslinate 

Downstream Products

• 1532556-50-5 (2α,3β)-bisacetyloxy-N-benzyl-olean-12-en-28-oic amide 
• 1532556-60-7 (E)-(3-phenyl)prop-2-enyl oxy-olean-12-en-28-oate 
• 4373-41-5 maslinic acid 
• 19533-95-0 (2α,3β) methyl 2,3-diacetyl-olean-12-en-28-oate 

Relevant academic research and scientific papers

Transformation of asiatic acid into a mitocanic, bimodal-acting rhodamine B conjugate of nanomolar cytotoxicity

Based on their biological activity natural products continue to represent optimal lead structures for the development of novel drug candidates. We focused on the syntheses of several derivatives of the triterpene asiatic acid and on the evaluation of their cytotoxic activity in a photometric sulforhodamin B assay. Especially, benzamide 2 and rhodamine B conjugate 11 show a distinct cytotoxicity for several human tumor cell lines, e.g. EC50 (A2780) = 110 ± 1 nM and EC50 (A2780) = 8 ± 2 nM, respectively. Interestingly, compound 11 showed for two human tumor cell lines (HT29 and 518A2) non-linear, bimodal dose-response relationships.

The cytotoxicity of oleanane derived aminocarboxamides depends on their aminoalkyl substituents

Several oligo-methylene diamine derived carboxamides of oleanolic and maslinic acid have been prepared, and substitutions of the terminal primary amine as well as variations of the length of alkyl chain of the diamine moiety were made. Biological evaluation of their cytotoxic activity was performed using photometric sulforhodamin B assays employing a panel of different human cancer cell lines. These experiments showed most of the carboxamides to be cytotoxic with EC50 values below 10 μM. Prolongation of the alkyl chain length initially reduced EC50 values to a minimum, but a decrease in cytotoxicity was observed for longer alkyl chains. Variation of substituents at the terminal nitrogen atom, however, did not influence EC50 values at all. Noteworthy results were obtained particularly for compounds 4, 6 and 23 as indicated by EC50 values lower than 2 μM, and in case of a maslinic derivative 23 even an increased tumor/non-tumor cell selectivity was observed. These compounds were further investigated using fluorescence microscopy and flow cytometry analysis, which revealed 6 to show indications of apoptosis.

Insect antifeedant compounds from Nothofagus dombeyi and N. pumilio

A bioassay-guided purification of the extracts of Nothofagus dombeyi and N. pumilio leaves yielded several triterpenes and flavonoids including 2-O-acetylmaslinic acid, 3-O-acetyl 20,24,25-trihydroxydammarane, and 3,20,24,25-tetrahydroxydammarane as new natural products. All the isolated compounds were assessed for antifeeding activity against the 5th instar larvae of Ctenopsteustis obliquana. 12-Hydroxyoleanolic lactone and pectolinarigenin from N. dombeyi and dihydrooroxylin A from N. pumilio, showed significant antifeeding activity.

Interaction between the anti-cancer drug diacetyl maslinic acid and bovine serum albumin: A biophysical study

Steady-state and time-resolved fluorescence, as well as Fourier transform-infrared (FT-IR) spectroscopy studies were made to understand the interaction between diacetyl maslinic acid (DMA) and bovine serum albumin (BSA) at pH 7.4. A decrease in fluorescence intensity and a blue shift of the emission peak were observed in the DMA-BSA complex, which were attributed to changes in the microenvironment of the protein fluorophores. Spectroscopic analysis revealed that the fluorescence-quenching mechanism between DMA and BSA was a static procedure. Displacement experiments with site markers indicated that DMA binds to BSA at Sudlow's site I (subdomain IIA). Binding constants for the protein-drug interaction were determined at three different temperatures (298, 305, and 310 K). Enthalpy (ΔH0) and entropy (ΔS0) changes indicated that hydrophobic interactions were the dominant intermolecular forces in the binding of DMA to BSA. The interaction appears to be entropy-driven, and the process spontaneous and endothermic. Enthalpy-entropy compensation suggests that reorganization of water molecules plays an important role. Anisotropy and FT-IR experiments revealed that BSA loses its structure in the presence of DMA. The secondary structure compositions of free BSA and DMA-BSA complex were determined by FT-IR. The binding distance and transfer efficiency for DMA-BSA complex were calculated according to the F?ster theory of non-radiative energy transfer.

MSBA-S – A pentacyclic sulfamate as a new option for radiotherapy of human breast cancer cells

Many pentacyclic triterpenoids show anti-cancer and anti-inflammatory properties. Recently, we detected a pronounced cytotoxicity and radiosensitivity of two betulinyl sulfamates in human breast cancer cells. Besides betulinic acid scaffold (BSBA-S), we synthesized several new sulfamate-coupled scaffolds from oleanolic acid (OSBA-S), ursolic acid (USBA-S), platanic acid (PSBA-S) and maslinic acid (MSBA-S). Highest cytotoxicity was monitored in breast cancer cell lines after MSBA-S treatment showing in SRB assays IC50 values between 3.7 μM and 5.8 μM. Other sulfamate/triterpene conjugates, however, were less cytotoxic holding IC50 values between 6.6 μM and >50 μM, respectively. MSBA-S-treated breast cancer cells displayed significantly reduced clonogenic survival and an increased rate of apoptosis as compared to the other conjugates. In addition, MSBA-S in combination with irradiation resulted in effects on radiosensitivity in MDA-MB-231 cells (DMF10 = 1.14). In particular, ROS formation was strongly assessed in MSBA-S-treated breast cancer cells. Our findings suggest that the sulfamate derivative of maslinic acid MSBA-S might be a new option for the radiation therapy in breast cancer cells.

Pentacyclic triterpene carboxylic acids derivatives integrated piperazine-amino acid complexes for α-glucosidase inhibition in vitro

Eighteen derivatives of pentacyclic triterpene carboxylic acids (Maslinic acid, Corosolic acid and Asiatic acid) have been prepared by coupling the piperazine complex of L-amino acids at the C-28 site of the parent compounds. The α-glucosidase inhibitory

Semi-synthesis of C28-modified triterpene acid derivatives from maslinic acid or corosolic acid as potential α-glucosidase inhibitors

Combining two bioactive moieties by covalent bond into a novel single hybrid biological entity in view of the principle of active splicing, twenty-two C28-modified derivatives of pentacyclic dihydroxytriterpene carboxylic acids with saturated nitrogen heterocycle segments (i.e. 1-deoxynojirimycin or piperazines) have been synthesized. The inhibitory activities of all final target compounds on α-glucosidase were evaluated in vitro. The results of α-glucosidase inhibition assay indicate that some derivatives (e.g. 4b: IC50 = 1468.4 μM; 12b: IC50 = 499.6 μM 12c: IC50 = 768.5 μM, 13c: IC50 = 819.2 μM) show superior inhibitory activity in α-glucosidase than that of the precursor maslinic acid (IC50 = 2540.6 μM) or corosolic acid (IC50 = 1363.7 μM), in which compound 12b (IC50 = 499.6 μM) possesses stronger inhibitory activity than that of acarbose (IC50 = 606 μM). In addition, the result of enzyme kinetics study reveals that the inhibitory mechanism of the compound 12b is non-competitive inhibition and the inhibition constant Ki is 570 μM. The binding interaction between compounds with α-glucosidase are predicted by molecular docking simulation.

Water-soluble maslinic acid derivative as well as preparation method and application thereof

The invention relates to a water-soluble maslinic acid derivative as well as a preparation method and application thereof, which belongs to the field of medicines. According to the water-soluble maslinic acid derivative provided by the invention, a series of hydrophilic amino acids are respectively introduced on maslinic acid C-28 carboxyl sites. Discovered from an experiment result, the hydrophilic property is significantly improved, and the glucose reduction activity of N(2alpha,3beta-dihydroxyl oleanane-12-ene-28-amide)-L-aspartic acid is apparently higher than that of a reference drug acarbose.

Synthesis of water soluble pentacyclic dihydroxyterpene carboxylic acid derivatives coupled amino acids and their inhibition activities on α-glucosidase

Twenty maslinic acid and corosolic acid derivatives were obtained by coupling with L-amino acids at C-28 position. The α-glucosidase inhibitory activities of the present compounds were evaluated in vitro. Results reveal that some of the derivatives exhibit a better α-glucosidase inhibitory activity than that of acarbose in the test conditions of ethanol-water solution and DMSO. It is worth noting that maslinic acid and corosolic acid derivatives coupled aspartic acid (9f: IC50 = 382 μm and 10f: IC50 = 364 μm, respectively) have the best water solubility and thus presented higher inhibitory activity than that of acarbose (IC50 = 484 μm). Unfortunately, all of the derivatives possess lower inhibitory properties of α-glucosidase than those of the parent compounds in the measurement system of DMSO solution, even if the derivatives exhibit better water solubility than that of the parent compounds.

Triterpene-based carboxamides act as good inhibitors of butyrylcholinesterase

A set of overall 40 carboxamides was prepared from five different natural occurring triterpenoids including oleanolic, ursolic, maslinic, betulinic, and platanic acid. All of which were derived from ethylene diamine holding an additional substituent connected to the ethylene diamine group. These derivatives were evaluated regarding their inhibitory activity of the enzymes acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) employing Ellman’s assay. We further determined the type of inhibition and inhibition constants. Carboxamides derived from platanic acid have been shown to be potent and selective BChE inhibitors. Especially the mixed-type inhibitor (3β)-N-(2-pyrrolidin-1-ylethyl)-3-acetyloxy-20-oxo-30-norlupan-28-amide (35) showed a remarkably low Ki of 0.07 ± 0.01 μM (Ki0 = 2.38 ± 0.48 μM) for the inhibition of BChE.