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Oleanolic acid (Synonyms: Astrantiagenin C, Caryophyllin, Giganteumgenin C, Gledigenin 1, NSC 114945, Oleanoic Acid, Virgaureagenin B)

Catalog No.GN10184

Oleanolic acid is a natural pentacyclic triterpenoid known for its effectiveness in treating hepatitis.

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Oleanolic acid Chemical Structure

Cas No.: 508-02-1

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10mM (in 1mL DMSO)
$35.00
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100mg
$27.00
In stock
500mg
$119.00
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Sample solution is provided at 25 µL, 10mM.

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Description of Oleanolic acid

Oleanolic acid is a natural pentacyclic triterpenoid known for its effectiveness in treating hepatitis. Additionally, it demonstrates antitumor effects across various types of cancers [1-3].

Oleanolic acid, at concentrations of 50 μM, 65 μM, and 80 μM, when administered for 24 or 48 hours, enhanced the ability of regorafenib to suppress the growth of PLC cells, particularly at doses of 65 μM or 80 μM[4]. Oleanolic acid, at concentrations of 2 μM, 4 μM, and 8 μM administered over 48 hours, acts as an activator of Nrf2. It exhibits a dose-dependent attenuation of TGF-β1-induced epithelial-mesenchymal transition (EMT) in NRK-52E cells [5]. Furthermore, oleanolic acid at a concentration of 50 μM, when applied for 6 hours, induces prostacyclin release in human coronary smooth muscle cells (SMC) through a Cox-2-dependent mechanism[6].

Oleanolic acid(50 mg/kg/d; i.g; 2weeks) exerts anti-EMT effect in vivo and enhances the antitumor effect of regorafenib[4]. Oleanolic acid(10-100 mg/kg; ip) demonstrated significant anti-epileptogenic potential in pentylenetetrazole-induced seizures[7].

References:

[1]. Pollier J, Goossens A. Oleanolic acid. Phytochemistry. 2012 May;77:10-5. doi: 10.1016/j.phytochem.2011.12.022. Epub 2012 Feb 28. PMID: 22377690.

[2]. Ma W, Wang DD, et,al. Caveolin-1 plays a key role in the oleanolic acid-induced apoptosis of HL-60 cells. Oncol Rep. 2014 Jul;32(1):293-301. doi: 10.3892/or.2014.3177. Epub 2014 May 15. PMID: 24842472.

[3]. Žiberna L, Šamec D, et,al. Oleanolic Acid Alters Multiple Cell Signaling Pathways: Implication in Cancer Prevention and Therapy. Int J Mol Sci. 2017 Mar 16;18(3):643. doi: 10.3390/ijms18030643. PMID: 28300756; PMCID: PMC5372655.

[4]. Wang H, Zhong W, et,al. Oleanolic Acid Inhibits Epithelial-Mesenchymal Transition of Hepatocellular Carcinoma by Promoting iNOS Dimerization. Mol Cancer Ther. 2019 Jan;18(1):62-74. doi: 10.1158/1535-7163.MCT-18-0448. Epub 2018 Oct 8. PMID: 30297361.

[5]. He WM, Yin JQ, et,al. Oleanolic acid attenuates TGF-β1-induced epithelial-mesenchymal transition in NRK-52E cells. BMC Complement Altern Med. 2018 Jul 4;18(1):205. doi: 10.1186/s12906-018-2265-y. PMID: 29973206; PMCID: PMC6031099.

[6]. Martínez-González J, Rodríguez-Rodríguez R, et,al. Oleanolic acid induces prostacyclin release in human vascular smooth muscle cells through a cyclooxygenase-2-dependent mechanism. J Nutr. 2008 Mar;138(3):443-8. doi: 10.1093/jn/138.3.443. PMID: 18287347.

[7]. Akünal Türel C, Yunusoğlu O. Oleanolic acid suppresses pentylenetetrazole-induced seizure in vivo. Int J Environ Health Res. 2023 May;33(5):529-540. doi: 10.1080/09603123.2023.2167947. Epub 2023 Feb 22. PMID: 36812380.

Protocol of Oleanolic acid

Cell experiment [1]:

Cell lines

PLC cells (Peritoneal lymphocytes (PLC-PRF-5))

Preparation method

PLC cells (5 × 103 cells/mL) were seeded in 96-well culture plates and incubated for 20 hours. Following this, the cells were treated with either solvent alone, oleanolic acid (at concentrations of 50 μM, 65 μM, and 80 μM), regorafenib, or a combination of oleanolic acid and regorafenib. The cells were then incubated for either 24 hours or 48 hours.

Reaction Conditions

50, 65, and 80 μM;24/48h

Applications

Oleanolic acid at doses of 65 μM or 80 μM enhanced the efficacy of regorafenib in suppressing the growth of PLC cells.

Animal experiment [1]:

Animal models

6-8week male BAlB/c nu/nu mice

Preparation method

1 × 106 PLC cells, suspended in PBS, were subcutaneously injected for inoculation into mice, who were then randomly divided into four groups. Two weeks post-inoculation, the experimental groups were orally administered oleanolic acid (50 mg/kg daily), regorafenib (10 mg/kg daily), or a combination of oleanolic acid (50 mg/kg daily) and regorafenib (10 mg/kg daily) for an additional 2 weeks. The control group received an equivalent volume of saline for the same duration.

Dosage form

50 mg/kg/d; i.g; 2weeks

Applications

Oleanolic acid treatment significantly inhibited the tumor growth. It can enhance the antitumor effect of regorafenib.

References:

[1].Wang H, Zhong W, et,al. Oleanolic Acid Inhibits Epithelial-Mesenchymal Transition of Hepatocellular Carcinoma by Promoting iNOS Dimerization. Mol Cancer Ther. 2019 Jan;18(1):62-74. doi: 10.1158/1535-7163.MCT-18-0448. Epub 2018 Oct 8. PMID: 30297361.

Chemical Properties of Oleanolic acid

Cas No. 508-02-1 SDF
Synonyms Astrantiagenin C, Caryophyllin, Giganteumgenin C, Gledigenin 1, NSC 114945, Oleanoic Acid, Virgaureagenin B
Chemical Name (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Canonical SMILES CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1)C)C(=O)O)C
Formula C30H48O3 M.Wt 456.71
Solubility ≥ 11.1mg/mL in DMSO Storage Store at 2-8°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of Oleanolic acid

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1 mg 5 mg 10 mg
1 mM 2.1896 mL 10.9479 mL 21.8957 mL
5 mM 0.4379 mL 2.1896 mL 4.3791 mL
10 mM 0.219 mL 1.0948 mL 2.1896 mL
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