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    Natural Products
    CAS No. 20069-09-4 Price $100 / 20mg
    Catalog No.CFN96137Purity>=98%
    Molecular Weight317.3Type of CompoundAlkaloids
    FormulaC17H19NO5Physical DescriptionPowder
    Download     COA    MSDSSimilar structuralComparison (Web)
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    According to end customer requirements, ChemFaces provide solvent format. This solvent format of product intended use: Signaling Inhibitors, Biological activities or Pharmacological activities.
    Size /Price /Stock 10 mM * 1 mL in DMSO / $35.9 / In-stock
    Other Packaging *Packaging according to customer requirements(100uL/well, 200uL/well and more), and Container use Storage Tube With Screw Cap
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  • Biological Activity
    Description: Piplartine shows potential anti-malaria, anti- leishmaniasis, anticancer, and mutagenic activities, it shows inhibitory activities of platelet aggregation induced by ADP and AA in vitro .
    Targets: P450 (e.g. CYP17) | Antifection
    In vitro:
    J Pharm Biomed Anal. 2014 Jul;95:113-20.
    In vitro metabolism of the alkaloid piplartine by rat liver microsomes.[Pubmed: 24667565]
    Because Piplartine (PPT) has demonstrated biological activities, such as cytotoxic, anxiolytic, antidepressant, antifungal and antiplatelet activities, this molecule is a relevant drug candidate. The metabolic fate of drug candidates is an essential requirement in assessing their safety and efficacy. Based on this requirement, the biotransformation of PPT by cytochrome P450 enzymes (CYP) was investigated for the first time.
    To determine the in vitro enzymatic kinetic parameters, an HPLC method was developed and validated to quantify PPT. All samples were separated on a reversed-phase C18 column using a mobile phase of acetonitrile:water (40:60, v/v). The method exhibited a linear range of 2.4-157.7 μmol/L, with the following calibration curve: y=0.0934 (±0.0010)x+0.0027, r=0.9975. The lower limit of quantitation was verified to be 2.4 μmol/L, with an RSD below 7%. The precision and accuracy were assessed for both within-day and between-day determinations; neither relative standard (RSD%) deviations nor relative errors (RER) exceeded a value of 15%. The mean absolute recovery was 85%, with an RSD value below 6%. The enzymatic kinetic parameters revealed a sigmoidal profile, with V(max)=4.7±0.3 μmol/mg mL⁻¹/min, h=2.5±0.4, S₅₀=44.7±0.3 μmol/L and CL(max)=0.054 μL/min/mg protein, indicating cooperativity behavior. Employing a mammalian model, PPT metabolism yielded two unreported monohydroxylated products (m/z 334). The identification and structural elucidation of the metabolites were performed by comparing their mass spectra with those spectra of the parent drug.
    For the first time, the in vitro metabolism studies employing microsomes were demonstrated to be a suitable tool for data regarding enzymatic kinetics and for the metabolites formed in the PPT mammalian metabolism.
    Planta Med. 2015 Jan;81(1):15-9.
    Antitumour efficacy of Piper tuberculatum and piplartine based on the hollow fiber assay.[Pubmed: 25519832 ]
    Piper tuberculatum, popularly known in Brazil as "jaborandi falso" and "pimenta darta", is widely used in folk medicine for the treatment of several diseases.
    In this study, the in vivo hollow fiber assay was used to investigate the antitumour efficacy of the crude extract and Piplartine obtained from P. tuberculatum roots. Human glioblastoma (SF-295) and colon carcinoma (HCT-8) cell lines were used. In vitro cytotoxicity was assayed by the MTT assay. In the hollow fiber assay, nude mice implanted with tumour cells in hollow fibers were treated for four consecutive days via the intraperitoneal route, and tumour cell populations were assessed by the MTT assay. Both the crude extract and Piplartine displayed cytotoxicity. In the hollow fiber assay, tumour growth inhibition rates were 24.6-54.8 % for the crude extract and 33.7-62.2 % for Piplartine. No signal of toxicity was noticed.
    In conclusion, the crude extract and Piplartine obtained from P. tuberculatum roots displayed in vitro and in vivo anticancer efficacy.
    Chem Biol Drug Des. 2016 Jun;87(6):833-40.
    Design, Synthesis and Pharmacological Evaluation of Novel Piperlongumine derivatives as Potential Antiplatelet Aggregation Candidate.[Pubmed: 26706668 ]

    A series of novel piperlongumine derivatives (4a-i, 6a-i) were designed and synthesized. The inhibitory activities of platelet aggregation induced by ADP and AA in vitro have been evaluated by bron turbidimetry and liver microsomal incubated assay.
    The assay results show that compounds 4e and 6e exhibited remarkable potency to that of the positive control Piplartine and aspirin.
    In vivo:
    Mutat Res. 2009 Jun-Jul;677(1-2):8-13.
    Piplartine induces genotoxicity in eukaryotic but not in prokaryotic model systems.[Pubmed: 19379832 ]
    Piplartine {5,6-dihydro-1-[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]-2(1H)-pyridinone} is an alkamide present in Piper species that exhibits promising anticancer properties. It was previously shown that Piplartine is mutagenic in yeast and cultured mammalian cells.
    This study was performed to increase the knowledge on the mutagenic potential of Piplartine using the Salmonella/microsome assay, V79 cell micronucleus and chromosome aberration assays, and mouse bone-marrow micronucleus tests. Piplartine was isolated from the roots of Piper tuberculatum. This extracted compound was unable to induce a mutagenic response in any Salmonella typhimurium strain either in the presence or absence of metabolic activation. Piplartine showed mutagenic effects in V79 cells, as there was an increased frequency of aberrant cells and micronuclei formation. In addition, Piplartine administered at 50mg/kg did not induce micronucleus formation in vivo, but a dose of 100mg/kg induced an increase in the levels of micronucleus polychromatic erythrocytes (MNPCEs).
    Overall, these results provide further support that Piplartine induces in vivo and in vitro mutagenicity in eukaryotic models.
    Piplartine Description
    Source: The herbs of Piper longum L.
    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 3.1516 mL 15.758 mL 31.5159 mL 63.0318 mL 78.7898 mL
    5 mM 0.6303 mL 3.1516 mL 6.3032 mL 12.6064 mL 15.758 mL
    10 mM 0.3152 mL 1.5758 mL 3.1516 mL 6.3032 mL 7.879 mL
    50 mM 0.063 mL 0.3152 mL 0.6303 mL 1.2606 mL 1.5758 mL
    100 mM 0.0315 mL 0.1576 mL 0.3152 mL 0.6303 mL 0.7879 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.
    Cell Research:
    Pharm Biol. 2017 Dec;55(1):1601-1607.
    Effect of piplartine and cinnamides on Leishmania amazonensis, Plasmodium falciparum and on peritoneal cells of Swiss mice.[Pubmed: 28415906 ]
    Plants of the Piperaceae family produce Piplartine that was used to synthesize the cinnamides. To assess the effects of Piplartine (1) and cinnamides (2-5) against the protozoa responsible for malaria and leishmaniasis, and peritoneal cells of Swiss mice.
    Cultures of Leishmania amazonensis, Plasmodium falciparum-infected erythrocytes, and peritoneal cells were incubated, in triplicate, with different concentrations of the compounds (0 to 256 μg/mL). The inhibitory concentration (IC50) in L. amazonensis and cytotoxic concentration (CC50) in peritoneal cell were assessed by the MTT method after 6 h of incubation, while the IC50 for P. falciparum-infected erythrocytes was determined by optical microscopy after 48 or 72 h of incubation; the Selectivity Index (SI) was calculated by CC50/IC50. All compounds inhibited the growth of microorganisms, being more effective against P. falciparum after 72 h of incubation, especially for the compounds 1 (IC50 = 3.2 μg/mL) and 5 (IC50 = 6.6 μg/mL), than to L. amazonensis (compound 1 = 179.0 μg/mL; compound 5 = 106.0 μg/mL). Despite all compounds reducing the viability of peritoneal cells, the SI were <10 to L. amazonensis, whereas in the cultures of P. falciparum the SI >10 for the Piplartine (>37.4) and cinnamides 4 (>10.7) and 5 (= 38.4).
    The potential of Piplartine and cinnamides 4 and 5 in the treatment of malaria suggest further pre-clinical studies to evaluate their effects in murine malaria and to determine their mechanisms in cells of the immune system.