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    Oleanolic acid
    Information
    CAS No. 508-02-1 Price $30 / 20mg
    Catalog No.CFN98800Purity>=98%
    Molecular Weight456.7 Type of CompoundTriterpenoids
    FormulaC30H48O3Physical DescriptionPowder
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    Oleanolic acid

    Oleanolic acid
    Product Name Oleanolic acid
    CAS No.: 508-02-1
    Catalog No.: CFN98800
    Molecular Formula: C30H48O3
    Molecular Weight: 456.7 g/mol
    Purity: >=98%
    Type of Compound: Triterpenoids
    Physical Desc.: Powder
    Targets: NO | TNF-伪 | IL Receptor | NOS | ERK | PI3K | Akt | HCV | BDNF | CREB | miR-132
    Source: The herbs of Boehmeria nivea (Linn.) Gaudich.
    Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
    Price: $30 / 20mg
    Inquire / Order: manager@chemfaces.com
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  • Br J Pharmacol.2018, 175(6):902-923
  • Biomolecules.2019, 9(11):E696
  • Nat Prod Sci.2016, 22(2)
  • Research Square2020, doi: 10.21203.
  • Molecules.2018, 23(11):E2837
  • Exp Parasitol.2018, 194:67-78
  • Front Pharmacol.2019, 10:1025
  • Biochem Biophys Res Commun.2020, 522(1):40-46
  • J Neuroinflammation.2020, 17(1):75.
  • Sci Rep.2019, 9:19059
  • Related Screening Libraries
    Size /Price /Stock 10 mM * 100 uL in DMSO / Inquiry / In-stock
    10 mM * 1 mL in DMSO / Inquiry / In-stock
    Related Libraries
  • Anticancer Compound Library
  • Anti-inflammatory Compound Library
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  • Triterpenoids Compound Library
  • TNF-α Inhibitor Library
  • PI3K Inhibitor Library
  • NOS Inhibitor Library
  • NO Inhibitor Library
  • IL Receptor Inhibitor Library
  • HCV Inhibitor Library
  • ERK Inhibitor Library
  • Akt Inhibitor Library
  • Biological Activity
    Description: Oleanolic acid is a non-toxic, hepatoprotective triterpenoid found in Phytolacca Americana, which exerts antitumor, anti-inflammatory, antioxidant, and antiviral properties. Oleanolic acid exhibits anti-HCV activity at least partly through suppressing HCV NS5B RdRp activity as a noncompetitive inhibitor; it induces the upregulation of miR-132, which serves as an important regulator of neurotrophic actions, mainly through the activation of the hippocampal BDNF-ERK-CREB signalling pathways; can be employed as a lead in the development of potent NO inhibitors. Oleanolic acid supplement ameliorates fructose-induced Adipo-IR in rats via the IRS-1/phosphatidylinositol 3-kinase/Akt pathway.
    Targets: NO | TNF-α | IL Receptor | NOS | ERK | PI3K | Akt | HCV | BDNF | CREB | miR-132
    In vitro:
    Bioorg Med Chem Lett. 2014 Sep 1;24(17):4114-9.
    Oleanolic acid analogs as NO, TNF-α and IL-1β inhibitors: synthesis, biological evaluation and docking studies.[Pubmed: 25113933]
    A series of Oleanolic acid analogs, characterized by structural modifications at position C-3 and C-28 of oleanane skeleton were synthesized and assessed for antiinflammatory potential towards lipopolysaccharide (LPS) induced nitric oxide (NO) production in macrophages.
    METHODS AND RESULTS:
    Results revealed that all the synthesized analogs of Oleanolic acid inhibit NO production with an IC50 of 2.66-41.7 μM as compared to the specific nitric oxide synthase (NOS) inhibitor, L-NAME (IC50=69.21 and 73.18 μM on RAW 264.7 and J774A.1 cells, respectively) without affecting the cell viability when tested at their half maximal concentration. The most potent NO inhibitors (2, 8, 9 and 10) at a concentration of 20 μg/mL also demonstrated mild inhibition (27.9-51.9%) of LPS-induced tumor necrosis factor alpha (TNF-α) and weak inhibition (11.1-37.5%) towards interleukin 1-beta (IL-1β) production in both the cells.
    CONCLUSIONS:
    The present study paves a direction that analogs of Oleanolic acid can be employed as a lead in the development of potent NO inhibitors. Molecular docking studies also showed that 10 (with top Goldscore docking pose 19.05) showed similar interaction as that of co-crystallized inhibitor and, thereby, helps to design the potent inhibitors of TNF-α.
    Antiviral Res. 2013 Apr;98(1):44-53.
    Oleanolic acid and ursolic acid: novel hepatitis C virus antivirals that inhibit NS5B activity.[Pubmed: 23422646 ]
    Hepatitis C virus (HCV) infects up to 170 million people worldwide and causes significant morbidity and mortality. Unfortunately, current therapy is only curative in approximately 50% of HCV patients and has adverse side effects, which warrants the need to develop novel and effective antivirals against HCV. We have previously reported that the Chinese herb Fructus Ligustri Lucidi (FLL) directly inhibited HCV NS5B RNA-dependent RNA polymerase (RdRp) activity (Kong et al., 2007).
    METHODS AND RESULTS:
    In this study, we found that the FLL aqueous extract strongly suppressed HCV replication. Further high-performance liquid chromatography (HPLC) analysis combined with inhibitory assays indicates that Oleanolic acid and ursolic acid are two antiviral components within FLL aqueous extract that significantly suppressed the replication of HCV genotype 1b replicon and HCV genotype 2a JFH1 virus. Moreover, Oleanolic acid and ursolic acid exhibited anti-HCV activity at least partly through suppressing HCV NS5B RdRp activity as noncompetitive inhibitors.
    CONCLUSIONS:
    Therefore, our results for the first time demonstrated that natural products Oleanolic acid and ursolic acid could be used as potential HCV antivirals that can be applied to clinic trials either as monotherapy or in combination with other HCV antivirals.
    Mol Cell Biochem . 2015 Feb;400(1-2):1-7.
    Oleanolic acid suppresses the proliferation of lung carcinoma cells by miR-122/Cyclin G1/MEF2D axis[Pubmed: 25472877]
    Oleanolic acid (OA) is a natural compound from plants with anti-tumor activities. However, the mechanism of the inhibitory effect of OA on cell cycle progression has not been completely explored. We employed several lung carcinoma cell lines to investigate the cell cycle-related molecular pathway affected by OA. The data revealed that OA suppressed the proliferation of lung cancer cells in both dose- and time-dependent manners, along with an increase in miR-122 abundance. The suppression of miR-122 abolished the effect of OA on lung cancer cells. CCNG1 and MEF2D, two putative miR-122 targets, were found to be downregulated by OA treatment. Restoring their expression counteracted the effect of OA on lung carcinoma cells. OA was further shown to induce the expression of miR-122-regulating transcriptional factors in lung cancer cells. Collectively, OA induced cell cycle arrest in lung cancer cells through miR-122/Cyclin G1/MEF2D pathway. This finding may contribute to the understanding of the molecular mechanism of OA's anti-tumor activity.
    J Nutr Biochem . 2014 Nov;25(11):1154-1160.
    Oleanolic acid inhibits proliferation and invasiveness of Kras-transformed cells via autophagy[Pubmed: 25172632]
    Oleanolic acid (OA) has been widely studied because of its pleiotropic therapeutic and preventive effect on various diseases. However, the mechanisms of OA's action are still not clear yet, especially its suppressing effect on transformed cells. In this work, we found that OA induced autophagy in normal tissue-derived cells without cytotoxicity. OA-induced autophagy was shown to decrease the proliferation of KRAS-transformed normal cells and to impair their invasion and anchorage-independent growth. Interrupting autophagy rescued OA's effect on the transformed cells. Mouse model experiments also demonstrated that OA suppressed the growth of KRAS-transformed breast epithelial cell MCF10A-derived tumor xenograft by inducing autophagy. Finally, we identified that OA induced autophagy in normal cells by inhibiting the activation of Akt/mTOR/S6K signaling. In conclusions, we found that OA treatment permitted normal cells to undergo autophagy. The induced autophagy was required for OA to prevent or delay the growth of transformed normal cells.
    In vivo:
    J Mol Cell Cardiol . 2014 Jul;72:250-62.
    Oleanolic acid modulates the immune-inflammatory response in mice with experimental autoimmune myocarditis and protects from cardiac injury. Therapeutic implications for the human disease[Pubmed: 24732212]
    Myocarditis and dilated cardiomyopathy (DCM) are inflammatory diseases of the myocardium, for which appropriate treatment remains a major clinical challenge. Oleanolic acid (OA), a natural triterpene widely distributed in food and medicinal plants, possesses a large range of biological effects with beneficial properties for health and disease prevention. Several experimental approaches have shown its cardioprotective actions, and OA has recently been proven effective for treating Th1 cell-mediated inflammatory diseases; however, its effect on inflammatory heart disorders, including myocarditis, has not yet been addressed. Therefore, the present study was undertaken to determine the effectiveness of OA in prevention and treatment of experimental autoimmune myocarditis (EAM). The utility of OA was evaluated in vivo through their administration to cardiac α-myosin (MyHc-α614-629)-immunized BALB/c mice from day 0 or day 21 post-immunization to the end of the experiment, and in vitro through their addition to stimulated-cardiac cells. Prophylactic and therapeutic administration of OA dramatically decreased disease severity: the heart weight/body weight ratio as well as plasma levels of brain natriuretic peptide and myosin-specific autoantibodies production were significantly reduced in OA-treated EAM animals, compared with untreated ones. Histological heart analysis showed that OA-treatment diminished cell infiltration, fibrosis and dystrophic calcifications. OA also decreased proliferation of cardiac fibroblast in vitro and attenuated calcium and collagen deposition induced by relevant cytokines of active myocarditis. Furthermore, in OA-treated EAM mice the number of Treg cells and the production of IL-10 and IL-35 were markedly increased, while proinflammatory and profibrotic cytokines were significantly reduced. We demonstrate that OA ameliorates both developing and established EAM by promoting an antiinflammatory cytokine profile and by interfering with the generation of cardiac-specific autoantibodies, as well as through direct protective effects on cardiac cells. Therefore, we envision this natural product as novel helpful tool for intervention in inflammatory cardiomyopathies including myocarditis.
    Oleanolic acid Description
    Source: The herbs of Boehmeria nivea (Linn.) Gaudich.
    Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
    Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

    Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

    Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com

    After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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    Calculate Dilution Ratios(Only for Reference)
    1 mg 5 mg 10 mg 20 mg 25 mg
    1 mM 2.1896 mL 10.9481 mL 21.8962 mL 43.7924 mL 54.7405 mL
    5 mM 0.4379 mL 2.1896 mL 4.3792 mL 8.7585 mL 10.9481 mL
    10 mM 0.219 mL 1.0948 mL 2.1896 mL 4.3792 mL 5.4741 mL
    50 mM 0.0438 mL 0.219 mL 0.4379 mL 0.8758 mL 1.0948 mL
    100 mM 0.0219 mL 0.1095 mL 0.219 mL 0.4379 mL 0.5474 mL
    * Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
    Protocol
    Kinase Assay:
    Toxicol Appl Pharmacol. 2014 Jun 1;277(2):155-63.
    Oleanolic acid supplement attenuates liquid fructose-induced adipose tissue insulin resistance through the insulin receptor substrate-1/phosphatidylinositol 3-kinase/Akt signaling pathway in rats.[Pubmed: 24704288]
    Oleanolic acid, a triterpenoid contained in more than 1620 plants including various fruits and foodstuffs, has numerous metabolic effects, such as hepatoprotection. However, its underlying mechanisms remain poorly understood. Adipose tissue insulin resistance (Adipo-IR) may contribute to the development and progress of metabolic abnormalities through release of excessive free fatty acids from adipose tissue.
    METHODS AND RESULTS:
    This study investigated the effect of Oleanolic acid on Adipo-IR. The results showed that supplement with Oleanolic acid (25 mg/kg, once daily, by oral gavage) over 10 weeks attenuated liquid fructose-induced increase in plasma insulin concentration and the homeostasis model assessment of insulin resistance (HOMA-IR) index in rats. Simultaneously, Oleanolic acid reversed the increase in the Adipo-IR index and plasma non-esterified fatty acid concentrations during the oral glucose tolerance test assessment. In white adipose tissue, Oleanolic acid enhanced mRNA expression of the genes encoding insulin receptor, insulin receptor substrate (IRS)-1 and phosphatidylinositol 3-kinase. At the protein level, Oleanolic acid upregulated total IRS-1 expression, suppressed the increased phosphorylated IRS-1 at serine-307, and restored the increased phosphorylated IRS-1 to total IRS-1 ratio. In contrast, phosphorylated Akt to total Akt ratio was increased. Furthermore, Oleanolic acid reversed fructose-induced decrease in phosphorylated-Akt/Akt protein to plasma insulin concentration ratio. However, Oleanolic acid did not affect IRS-2 mRNA expression.
    CONCLUSIONS:
    Therefore, these results suggest that Oleanolic acid supplement ameliorates fructose-induced Adipo-IR in rats via the IRS-1/phosphatidylinositol 3-kinase/Akt pathway. Our findings may provide new insights into the mechanisms of metabolic actions of Oleanolic acid.
    Cell Research:
    Anticancer Res. 2014 Aug;34(8):4135-9.
    Semi-synthesis of nitrogen derivatives of oleanolic acid and effect on breast carcinoma MCF-7 cells.[Pubmed: 25075040 ]
    Oleanolic acid is a triterpenoid that has shown in vitro cytotoxic activity against human tumour cells and is known to be present in many higher plants.
    METHODS AND RESULTS:
    Oleanolic acid is known to have some biological potential including anticancer property. Oleanolic acid was isolated from the ethyl acetate fraction of Syzygium aromaticum seed with an aim of dervitatising the functional group and evaluating the biological activities of the semi-synthesised compounds. Acylation of the alcohol functional group of the Oleanolic acid afforded the opportunity of hydrazine reaction to give 3-acetoleanolic hydrazide. Further reaction of 3-acetoleanolic hydrazide with benzyladehyde, glacial acetic acid and methanol resulted in the synthesis of the corresponding 3-acetoxyoleanolic hydrazone. The semi-synthetic Oleanolic acid derivatives did not exhibit enhanced cytotoxic activity over Oleanolic acid itself.
    CONCLUSIONS:
    3-acetoxyoleanolic hydrazide has a potent anticancer activity.
    Animal Research:
    J Psychiatry Neurosci. 2014 Sep;39(5):348-59.
    BDNF-ERK-CREB signalling mediates the role of miR-132 in the regulation of the effects of oleanolic acid in male mice.[Pubmed: 25079084]
    Although previous study has demonstrated that brain-derived neurotrophic factor (BDNF) is involved in the antidepressant-like effect of Oleanolic acid, there is little information regarding the details of the molecular mechanism involved in this effect.
    METHODS AND RESULTS:
    We used a chronic unpredictable mild stress (CUMS) model to test the antidepressant-like effect of Oleanolic acid on depressant-like behaviour, miR-132 expression and synaptic protein expression in the male mouse hippocampus. Furthermore, we explored the possible signalling pathways associated with miR-132 expression that mediate the effect of Oleanolic acid on neuronal proliferation. The results demonstrated that a 3-week treatment with Oleanolic acid ameliorated CUMS-induced anhedonic and anxiogenic behaviours. Furthermore, we found that Oleanolic acid led to the BDNF-related phosphorylation and activation of extracellular signal-regulated kinases (ERK) and cyclic adenosine monophosphate response element binding protein (CREB), which was associated with the upregulation of miR-132 and hippocampal neuronal proliferation. Moreover, experiments with an miR-132 antagomir revealed that targeting miR-132 led to inhibition of neuronal proliferation and the postsynaptic density protein 95, but did not affect presynaptic protein synapsin I. Several other stimuli can also induce CREB phosphorylation in the hippocampus. Thus, regulation of miR-132 may not be restricted to neurotrophic signalling.
    CONCLUSIONS:
    Our results show that Oleanolic acid induces the upregulation of miR-132, which serves as an important regulator of neurotrophic actions, mainly through the activation of the hippocampal BDNF-ERK-CREB signalling pathways.
    Structure Identification:
    Phytochemistry. 2012 May;77:10-5.
    Oleanolic acid.[Pubmed: 22377690 ]
    Oleanolic acid (3β-hydroxyolean-12-en-28-oic acid) is a pentacyclic triterpenoid compound with a widespread occurrence throughout the plant kingdom. In nature, the compound exists either as a free acid or as an aglycone precursor for triterpenoid saponins, in which it can be linked to one or more sugar chains. Oleanolic acid and its derivatives possess several promising pharmacological activities, such as hepatoprotective effects, and anti-inflammatory, antioxidant, or anticancer activities. With the recent elucidation of its biosynthesis and the imminent commercialization of the first Oleanolic acid-derived drug, the compound promises to remain important for various studies.
    CONCLUSIONS:
    In this review, the recent progress in understanding the Oleanolic acid biosynthesis and its pharmacology are discussed. Furthermore, the importance and potential application of synthetic Oleanolic acid derivatives are highlighted, and research perspectives on Oleanolic acid are given.
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