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    Lupenone
    Information
    CAS No. 1617-70-5 Price $178 / 10mg
    Catalog No.CFN99681Purity>=98%
    Molecular Weight424.7 Type of CompoundTriterpenoids
    FormulaC30H48OPhysical DescriptionWhite powder
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    Lupenone

    Lupenone
    Product Name Lupenone
    CAS No.: 1617-70-5
    Catalog No.: CFN99681
    Molecular Formula: C30H48O
    Molecular Weight: 424.7 g/mol
    Purity: >=98%
    Type of Compound: Triterpenoids
    Physical Desc.: White powder
    Targets: PPAR | ERK | MAPK | Antifection | PTP1B
    Source: The roots of Pueraria thomsonii Benth.
    Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
    Price: $178 / 10mg
    Inquire / Order: manager@chemfaces.com
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  • J Formos Med Assoc.2020, S0929-6646(20)30425-3
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  • 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
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  • Biological Activity
    Description: Lupenone and lupeol inhibit protein tyrosine phosphatase 1B (PTP1B) with IC50 values of 13.7 ± 2.1 and 5.6 ± 0.9 uM, respectively, they are non−competitive inhibitors of PTP1B, and PTP1B appears to be an attractive target for the development of new drugs for type 2 diabetes and obesity. Lupenone stimulates melanogenesis by increasing the tyrosinase enzyme expression via mitogen-activated protein kinase phosphorylated extracellular signal-regulated kinases 1 and 2 phosphorylation inhibition. A 1 : 4 mixture of Lupenone and caryophyllene oxide shows trypanocidal activity.
    Targets: PPAR | ERK | MAPK | Antifection | PTP1B
    In vitro:
    Phytother Res. 2013 May;27(5):761-6.
    Lupenone isolated from Adenophora triphylla var. japonica extract inhibits adipogenic differentiation through the downregulation of PPARγ in 3T3-L1 cells.[Pubmed: 22848028]
    Adenophora triphylla var. japonica (Campanulaceae) is known to have anti-inflammatory and anti-tussive effects. Dysfunction of adipocytes and adipose tissue in obesity is related to various inflammatory cytokines or adipokines.
    METHODS AND RESULTS:
    In this study, we investigated whether Lupenone isolated from A. triphylla var. japonica extract inhibits adipocyte differentiation and expression of adipogenic marker genes in 3T3-L1 preadipocytes. We demonstrated that Lupenone resulted in a significant reduction in lipid accumulation and expression of adipogenic marker genes in a dose-dependent manner. In addition, Lupenone decreased the transcriptional activity of peroxisome proliferator-activated receptor γ (PPARγ) induced by troglitazone, and we also demonstrated that Lupenone suppressed the PPARγ and CCAAT-enhancer-binding protein α (C/EBPα) protein levels.
    CONCLUSIONS:
    These findings demonstrated that Lupenone isolated from A. triphylla var. japonica extract effectively inhibited adipocyte differentiation through downregulation of related transcription factor, particularly the PPARγ gene.
    Evid Based Complement Alternat Med. 2013;2013:435398.
    Synergistic Effect of Lupenone and Caryophyllene Oxide against Trypanosoma cruzi.[Pubmed: 23762135]
    The in vitro trypanocidal activity of a 1 : 4 mixture of Lupenone and caryophyllene oxide confirmed a synergistic effect of the terpenoids against epimastigotes forms of T. cruzi (IC50 = 10.4  μ g/mL, FIC = 0.46). In addition, testing of the terpenoid mixture for its capacity to reduce the number of amastigote nests in cardiac tissue and skeletal muscle of infected mice showed a reduction of more than 80% at a dose level of 20.8 mg·kg(-1)·day(-1).
    Biomed Pharmacother . 2018 Jul;103:198-203.
    Beneficial health effects of lupenone triterpene: A review[Pubmed: 29653365]
    Abstract There are a large number of new structure compounds with good pharmacological activity in the natural plants, can be applied to the treatment of human diseases. Finding active ingredients from the plants is one of the important ways to develop new drugs. Triterpenes are widespread in plants, and Lupenone belongs to lupane type triterpenoids. Lupenone is very common natural ingredient distributed in multi-family plants including Asteraceae, Balanophoraceae, Cactaceae, Iridaceae, Musaceae, Urticaceae, Leguminosae, Bombacaceae, etc., but its distribution has no regular. The consumption of Lupenone in vegetarian diet is high in human life. Pharmacological screening of Lupenone revealed various pharmacological activities including anti-inflammatory, anti-virus, anti-diabetes, anti-cancer, improving Chagas disease without major toxicity. Based on these important pharmacological activities, this review provides detailed account of pre-clinical studies conducted to determine the utility of Lupenone as a therapeutic and chemopreventive agent for the treatment of various diseases. Keywords: Chagas disease; Diabetes; Inflammation; Lupenone; Tumor; Virus.
    In vivo:
    Mol Divers . 2020 Feb;24(1):21-30.
    Lupenone is a good anti-inflammatory compound based on the network pharmacology[Pubmed: 30796639]
    Abstract The dried rhizome of Musa basjoo Sieb. et Zucc. is Rhizoma Musae. It has been used to treat diabetes in Miao medicine in China. Lupenone was isolated from Rhizoma Musae and has good anti-diabetic activity. Its mechanism of action is unclear. Diabetes is a chronic low-level systemic inflammatory disease, and Lupenone has anti-inflammatory activity, but the underlying mechanism is not fully elucidated. In this study, we aimed to construct the drug-target biologic network and predict the anti-inflammatory mechanism of Lupenone. The network-based pharmacologic analysis platform was used to identify the target proteins related to inflammation. Furthermore, the effects of Lupenone on acute, subacute and diabetic pancreatic inflammation were evaluated. The "component-target-disease" network was constructed using Cytoscape. Lupenone could regulate transcription factor p65, NF-kappa-B inhibitor alpha, transcription factor AP-1, NF-kappa-B essential modulator, nuclear factor NF-kappa-B p105 subunit, epidermal growth factor receptor, hypoxia-inducible factor 1-alpha and other proteins related to the PI3K-Akt, Toll-like receptor and NF-kappa B signaling pathways. In addition, Lupenone significantly decreased acute and subacute inflammation in mice as well as the IL-1β and IFN-γ levels in the pancreas of diabetic rats. The above results provide strong support for studying the molecular mechanism of Lupenone in the treatment of diabetes from the perspective of anti-inflammation. Keywords: Diabetes; Inflammation; Lupenone; Network pharmacology; Pancreas; Target.
    Lupenone Description
    Source: The roots of Pueraria thomsonii Benth.
    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 2.3546 mL 11.773 mL 23.546 mL 47.0921 mL 58.8651 mL
    5 mM 0.4709 mL 2.3546 mL 4.7092 mL 9.4184 mL 11.773 mL
    10 mM 0.2355 mL 1.1773 mL 2.3546 mL 4.7092 mL 5.8865 mL
    50 mM 0.0471 mL 0.2355 mL 0.4709 mL 0.9418 mL 1.1773 mL
    100 mM 0.0235 mL 0.1177 mL 0.2355 mL 0.4709 mL 0.5887 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:
    Planta Med. 2013 Mar;79(3-4):236-43.
    Lupenone from Erica multiflora leaf extract stimulates melanogenesis in B16 murine melanoma cells through the inhibition of ERK1/2 activation.[Pubmed: 23408272]
    Hypopigmentation diseases are usually managed using UVB light which increases the patients' risk for skin cancer. Here, we evaluated the melanogenesis stimulatory effects of leaf extracts of Erica multiflora, a medicinal plant from the Mediterranean region, and its active component, lup-20(29)-en-3-one, as possible therapeutic agents to address hypopigmentation disorders.
    METHODS AND RESULTS:
    B16 murine melanoma cells were treated with E. multiflora extracts or its active component Lupenone to evaluate their effects on melanin biosynthesis. The mechanism underlying the observed effects was also determined. Bioactivity-guided fractionation of fifteen ethyl acetate fractions identified fraction 2 to have melanogenesis stimulatory effects due to its ability to decrease mitogen-activated protein kinase phosphorylated extracellular signal-regulated kinases 1 and 2 activation. Preparative TLC of ethyl acetate fraction 2 revealed the presence of lup-20(29)-en-3-one as the major bioactive component. B16 cells treated with lup-20(29)-en-3-one increased melanin content without cytotoxicity. To determine the mechanism for the observed effects of lup-20(29)-en-3-one, the tyrosinase enzyme activity, the tyrosinase protein expression, and the activation of phosphorylated extracellular signal-regulated kinases 1 and 2 were determined. In addition, the expression of the tyrosinase mRNA was quantified using real-time PCR. Results showed that lup-20(29)-en-3-one has no effect on the tyrosinase enzyme activity but can increase tyrosinase expression at both the transcriptional and translational levels. The increase in the tyrosinase mRNA expression was most likely due to the inhibited mitogen-activated protein kinase phosphorylated extracellular signal-regulated kinases 1 and 2 activation.
    CONCLUSIONS:
    We report for the first time that E. multiflora ethyl acetate extract and its active compound lup-20(29)-en-3-one stimulate melanogenesis by increasing the tyrosinase enzyme expression via mitogen-activated protein kinase phosphorylated extracellular signal-regulated kinases 1 and 2 phosphorylation inhibition, making it a possible treatment for hypopigmentation diseases.
    J Enzyme Inhib Med Chem. 2009 Aug;24(4):1056-9.
    Inhibition of protein tyrosine phosphatase 1B by lupeol and lupenone isolated from Sorbus commixta.[Pubmed: 19548777 ]
    Protein tyrosine phosphatase 1B (PTP1B) appears to be an attractive target for the development of new drugs for type 2 diabetes and obesity.
    METHODS AND RESULTS:
    In our preliminary test, a MeOH extract of the stem barks of Sorbus commixta Hedl. (Rosaceae) showed strong PTP1B inhibitory activity. Bioassay-guided fractionation of the MeOH extract resulted in the isolation of two lupane-type triterpenes, Lupenone (1) and lupeol (2). Compounds 1 and 2 inhibited PTP1B with IC(50) values of 13.7 +/- 2.1 and 5.6 +/- 0.9 microM, respectively.
    CONCLUSIONS:
    Kinetic studies revealed that both the compounds 1 and 2 are non-competitive inhibitors of PTP1B that decrease V(max) values with no effect on K(m) values.
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