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ProductsBack/Piperlongumine [20069-09-4]
Chemical Structure
Chemical Structure
Chemical Structure

Piperlongumine [20069-09-4]

Research Use Only
AG-CN2-0024
AdipoGen Life Sciences
CAS Number20069-09-4
DownloadMSDS
Product group Chemicals
Estimated Purity>97%
Molecular Weight317.3
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    Piperlongumine [20069-09-4]
  • Delivery Days Customer
    10
  • CAS Number
    20069-09-4
  • Certification
    Research Use Only
  • Estimated Purity
    >97%
  • Molecular Formula
    C17H19NO5
  • Molecular Weight
    317.3
  • Scientific Description
    Chemical. CAS: 20069-09-4. Formula: C17H19NO5. MW: 317.3. Isolated from Piper longum roots. Cytotoxic against tumor cell lines. Induces necrosis and apoptosis in cancer cells. Shows anti-platelet aggregation activity possibly by inhibition of cyclooxgenase activity and a decrease in thromboxane A2 formation. Shows significant anxiolytic and antidepressant activities. Promotes adipogenesis of 3T3-L1 cells. Induces in vivo and in vitro mutagenicity in eukaryotic models. Selectively kills cancer cells by targeting the stress response to ROS. Shows in vitro schistosomicidal activity. - Cytotoxic against tumor cell lines [3, 4, 5]. Induces necrosis and apoptosis in cancer cells [5, 9, 12]. Shows anti-platelet aggregation activity possibly by inhibition of cyclooxgenase activity and a decrease in thromboxane A2 formation [4, 6, 10]. Shows significant anxiolytic and antidepressant activities [7]. Promotes adipogenesis of 3T3-L1 cells [8]. Induces in vivo and in vitro mutagenicity in eukaryotic models [11]. Selectively kills cancer cells by targeting the stress response to ROS [12]. Shows in vitro schistosomicidal activity [13]. Selective inhibitor of human immunoproteasome. Targets the beta5i subunit (LMP7) (IC50=15microM) with minimal inhibition of human constitutive proteasome [14].
  • SMILES
    COC1=CC(\C=C\C(=O)N2CCC=CC2=O)=CC(OC)=C1OC
  • Storage Instruction
    2°C to 8°C,-20°C
  • UNSPSC
    12352200

References

  • Alkaloids of Piper longum Linn. I. Structure and synthesis of piperlongumine and piperlonguminine: A. Chatterjee & C.P Dutta; Tetrahedron 23, 1769 (1967)
  • Cytotoxic pyridone alkaloids from the leaves of Piper aborescens: C.Y. Duh, et al.; J. Nat. Prod. 53, 1575 (1990)
  • Antiproliferative effects of two amides, piperine and piplartine, from Piper species: D.P. Bezerra, et al.; Z. Naturforsch. C 60, 539 (2005)
  • New cytotoxic cyclobutanoid amides, a new furanoid lignan and anti-platelet aggregation constituents from Piper arborescens: I.L. Tsai, et al.; Planta Med. 71, 535 (2005)
  • Piplartine induces inhibition of leukemia cell proliferation triggering both apoptosis and necrosis pathways: D.P. Bezerra, et al.; Toxicol. In Vitro 21, 1 (2007)
  • Piperlongumine, a constituent of Piper longum L. inhibits rabbit platelet aggregation as a thromboxane A(2) receptor antagonist: M. Iwashita, et al.; Eur. J. Pharmacol. 570, 38 (2007)
  • Piplartine, an amide alkaloid from Piper tuberculatum, presents anxiolytic and antidepressant effects in mice: F.F. Cícero Bezerra, et al.; Phytomedicine 14, 605 (2007)
  • Effects of amide constituents from pepper on adipogenesis in 3T3-L1 cells: H. Zhang, et al.; Bioorg. Med. Chem. Lett. 18, 3272 (2008)
  • Piplartine induces caspase-mediated apoptosis in PC-3 human prostate cancer cells: E.H. Kong, et al.; Oncol. Rep. 20, 785 (2008)
  • Antiplatelet effects of piplartine, an alkamide isolated from Piper tuberculatum: possible involvement of cyclooxygenase blockade and antioxidant activity: J.B. Fontenele, et al.; J. Pharm. Pharmacol. 61, 511 (2009)