An alkaloid with diverse biological activities
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Piperlongumine

Item No. 11006

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5,6-dihydro-1-[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]-2(1H)-pyridinone
CAS Number
20069-09-4
Synonyms
  • Piplartine
Molecular Formula
C17H19NO5
Formula Weight
317.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlDMSO:PBS (pH 7.2) (1:10): 0.1 mg/mlEthanol: 0.15 mg/ml
λmax
221, 327 nm
SMILES
COC(C(OC)=C1)=C(OC)C=C1/C=C/C(N2C(C=CCC2)=O)=O
InChi Code
InChI=1S/C17H19NO5/c1-21-13-10-12(11-14(22-2)17(13)23-3)7-8-16(20)18-9-5-4-6-15(18)19/h4,6-8,10-11H,5,9H2,1-3H3/b8-7+
InChi Key
VABYUUZNAVQNPG-BQYQJAHWSA-N
Origin
Plant/Piper longum
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

    $49

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    100 mg

    $171

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    500 mg

    $561

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    1 g

    $1,030

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Piperlongumine is an alkaloid that has been found in P. longum and has diverse biological activities.1,2,3 It binds to the TP receptor (Ki = 7.6 µM) and inhibits platelet aggregation induced by U-46619 (Item No. 16450) in washed isolated rabbit platelets.1 Piperlongumine also binds to thioredoxin reductase 1 (TrxR1) and glutathione S-transferase pi 1 (GSTP1; Kds = 22.2 and 133 µM, respectively), inhibits TrxR1 activity, induces apoptosis and reactive oxygen species (ROS) production in SGC-7901 gastric cancer cells, and reduces tumor volume and weight in an SGC-7901 mouse xenograft model.2 It reduces plasma glucose levels, as well as plasma and pancreatic levels of thiobarbituric acid reactive substances (TBARS) and lipid hydroperoxides, in a rat model of diabetes induced by streptozotocin (Item No. 13104).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Iwashita, M., Oka, N., Ohkubo, S., et al. Piperlongumine, a constituent of Piper longum L., inhibits rabbit platelet aggregation as a thromboxane A2 receptor antagonist. Eur. J. Pharmacol. 570(1-3), 38-42 (2007).

    2. Zou, P., Xia, Y., Ji, J., et al. Piperlongumine as a direct TrxR1 inhibitor with suppressive activity against gastric cancer. Cancer Lett. 375(1), 114-126 (2016).

    3. Xu, P., Xiao, J., and Chi, S. Piperlongumine attenuates oxidative stress, inflammatory, and apoptosis through modulating the GLUT-2/4 and AKT signaling pathway in streptozotocin-induced diabetic rats. J. Biochem. Mol. Toxicol. 35(6), 1-12 (2021).