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    Piperlonguminine
    Piperlonguminine
    Information
    CAS No. 5950-12-9 Price $188 / 5mg
    Catalog No.CFN91121Purity>=98%
    Molecular Weight273.3Type of CompoundAlkaloids
    FormulaC16H19NO3Physical DescriptionPowder
    Download     COA    MSDSSimilar structuralComparison (Web)
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    * Packaging according to customer requirements(5mg, 10mg, 20mg and more). We shipped via FedEx, DHL, UPS, EMS and others courier.
    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 / $131.6 / In-stock
    Other Packaging *Packaging according to customer requirements(100uL/well, 200uL/well and more), and Container use Storage Tube With Screw Cap
    Our products had been exported to the following research institutions and universities, And still growing.
  • University of Wisconsin-Madison (USA)
  • Nicolaus Copernicus Uniwersity (Poland)
  • Vin?a Institute of Nuclear Scie... (Serbia)
  • Shanghai Institute of Biochemis... (China)
  • National Cancer Institute (USA)
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  • St. Jude Children Research Hosp... (USA)
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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
  • Alkaloids Compound Library
  • Antifection Inhibitor Library
  • Biological Activity
    Description: Piperlonguminine is an efficient depigmenting agent with a novel mechanism of action. It has potent antitumor, antitrypanosomal, anti-hyperlipidemic, anti-platelet and anti-melanogenesis activities. Piperlonguminine obviously improves hepatocyte fatty degeneration of alcoholic fatty liver in mice, it can effectively prevent the occurrence and development of alcoholic fatty liver.
    Targets: Antifection
    In vitro:
    Pigment Cell Res. 2006 Feb;19(1):90-8.
    Inhibitory effect of piperlonguminine on melanin production in melanoma B16 cell line by downregulation of tyrosinase expression.[Pubmed: 16420250 ]
    Tyrosinase is a key enzyme for melanin biosynthesis, and hyperpigmentation disorders are associated with abnormal accumulation of melanin pigments, which can be improved by treatment with depigmenting agents.
    METHODS AND RESULTS:
    In the present study, Piperlonguminine from Piper longum was discovered to inhibit melanin production in melanoma B16 cells stimulated with alpha-melanocyte stimulating hormone (alpha-MSH), 3-isobutyl-1-methylxanthine or protoporphyrin IX, where the compound exhibited stronger depigmenting efficacy than kojic acid. However, Piperlonguminine did not affect 1-oleoyl-2-acetyl-sn-glycerol-induced melanogenesis and did not affect protein kinase C-mediated melanin production. Surprisingly, Piperlonguminine did not inhibit the catalytic activity of cell-free tyrosinase from melanoma B16 cells but rather suppressed tyrosinase mRNA expression. This effect was attributed to the inhibitory action of Piperlonguminine on alpha-MSH-induced signaling through cAMP to the cAMP responsive element binding protein that in turn regulates the expression of the microphthalmia-associated transcription factor, a key activator of the tyrosinase promoter.
    CONCLUSIONS:
    This study demonstrates that Piperlonguminine is an efficient depigmenting agent with a novel mechanism of action.
    Acta Trop. 2013 Mar;125(3):349-56.
    The natural compounds piperovatine and piperlonguminine induce autophagic cell death on Trypanosoma cruzi.[Pubmed: 23228524 ]
    The currently available treatments for Chagas disease show limited therapeutic potential and are associated with serious side effects. Our group has been attempting to find alternative drugs isolated from natural products as a potential source of pharmacological agents against Trypanosoma cruzi.
    METHODS AND RESULTS:
    Here, we demonstrate the antitrypanosomal activity of the amides piperovatine and Piperlonguminine isolated from Piper ovatum against epimastigotes and intracellular amastigotes. We also investigated the mechanisms of action of these compounds on extracellular amastigote and epimastigote forms of T. cruzi. These amides showed low toxicity to LLCMK(2) mammalian cells. By using transmission and scanning electron microscopy, we observed that the compounds caused severe alterations in T. cruzi. These alterations were mainly located in plasma membrane and mitochondria. Furthermore, the study of treated parasites labeled with Rh123, PI and MDC corroborate with our TEM data. These mitochondrial dysfunctions induced by the amides might trigger biochemical alterations that lead to cell death.
    CONCLUSIONS:
    Altogether, our data evidence a possible autophagic process.
    In vivo:
    Journal of Applied Toxicology, 2008, 28(5):599-607.
    In vivo growth inhibition of sarcoma 180 by piperlonguminine, an alkaloid amide from the Piper species.[Pubmed: 17975786]
    Many authors have already emphasized that phytochemicals from spices have biological applications. Piperlonguminine is a known alkaloid amide from peppers, including Piper divaricatum. The aim of this study was to investigate the in vitro and in vivo antitumor effects of Piperlonguminine in experimental models. In order to evaluate the toxicological aspects related to Piperlonguminine treatment, hematological, biochemical, histopathological and morphological analyses of treated animals were performed.
    METHODS AND RESULTS:
    Piperlonguminine did not show any significant in vitro cytotoxic effect at experimental exposure levels, but showed an in vivo antitumor effect. After 7 days of treatment, the inhibition rates were 38.71% and 40.68% at doses of 25 mg kg(-1) and 50 mg kg(-1), respectively. The histopathological analysis suggests that the liver and kidney were only weakly affected by Piperlonguminine treatment. Neither the enzymatic activity of transaminases (AST and ALT) nor the urea levels were significantly altered. In the hematological analysis, all parameters analysed remained constant after Piperlonguminine treatment.
    CONCLUSIONS:
    In conclusion, these data reinforce the anticancer potential of spice components.
    Piperlonguminine Description
    Source: The fruits of Piper nigrum 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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    Recently, ChemFaces products have been cited in many studies from excellent and top scientific journals

    Cell. 2018 Jan 11;172(1-2):249-261.e12.
    doi: 10.1016/j.cell.2017.12.019.
    IF=36.216(2019)

    PMID: 29328914

    Cell Metab. 2020 Mar 3;31(3):534-548.e5.
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    ACS Nano. 2018 Apr 24;12(4): 3385-3396.
    doi: 10.1021/acsnano.7b08969.
    IF=13.903(2019)

    PMID: 29553709

    Nature Plants. 2016 Dec 22;3: 16206.
    doi: 10.1038/nplants.2016.205.
    IF=13.297(2019)

    PMID: 28005066

    Sci Adv. 2018 Oct 24;4(10): eaat6994.
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    IF=12.804(2019)

    PMID: 30417089
    Calculate Dilution Ratios(Only for Reference)
    1 mg 5 mg 10 mg 20 mg 25 mg
    1 mM 3.659 mL 18.2949 mL 36.5898 mL 73.1797 mL 91.4746 mL
    5 mM 0.7318 mL 3.659 mL 7.318 mL 14.6359 mL 18.2949 mL
    10 mM 0.3659 mL 1.8295 mL 3.659 mL 7.318 mL 9.1475 mL
    50 mM 0.0732 mL 0.3659 mL 0.7318 mL 1.4636 mL 1.8295 mL
    100 mM 0.0366 mL 0.1829 mL 0.3659 mL 0.7318 mL 0.9147 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
    Animal Research:
    Food Science, 2014.
    Preventive Effects of Piperlonguminine on Alcoholic Fatty Liver Disease in Mice.[Reference: WebLink]
    This study aimed to investigate the preventive and therapeutic effects of Piperlonguminine(GBN) on alcoholic fatty liver disease(AFLD) in mice.
    METHODS AND RESULTS:
    Adult male Kunming mice were randomly divided into four groups: normal control, model, GBN low dose and high dose groups. The mice in normal control group were fed with a normal diet, and those in the other groups were fed with high-fat diet, and, at the same time, administered with alcohol daily at a level of 0.8 mL/30 g bw. The mice in GBN low and high dose groups were intragastrically administered with 0.8 mL/30 g bw of GBN at doses of 10 and 40 mg/(kg·d), respectively, and the normal control and model groups were given equal volume of distilled water, continuously for 6 weeks. After 12 h of fasting following the last administration, all the mice were sacrificed for the measurement of liver index, aspartate transaminase(AST), alanine transaminase(ALT), total cholesterol(TC) and triglyceride(TG) levels in serum and the pathological histological observation of liver tissue. Compared with the model group, the low and high dose groups significantly decreased liver index to(4.42 ± 0.50)% and(4.53 ± 0.44)%, respectively. Also, the levels of AST, ALT, TC and TG in serum were significantly decreased(P 0.01). And pathological histology showed that GBN obviously improved hepatocyte fatty degeneration of alcoholic fatty liver in mice.
    CONCLUSIONS:
    In conclusion, GBN can effectively prevent the occurrence and development of alcoholic fatty liver.