Piperlongumine

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Piperlongumine
Piperlongumine.svg
Names
IUPAC name
1-[(2E)-3-(3,4,5-Trimethoxyphenyl)prop-2-enoyl]-5,6-dihydropyridin-2(1H)-one
Other names
Piplartine
Identifiers
3D model (JSmol)
ChemSpider
Properties
C17H19NO5
Molar mass 317.34 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Piperlongumine (PL) is a natural product constituent of the fruit of the Long pepper (Piper longum),[1] a pepper plant found in southern India and southeast Asia.

Piperlongumine may have anti-cancer properties. In in vitro experiments, it selectively kills some types cancer cells over normal cells.[1] One study in a xenograft mouse model of cancer showed that piperlongumine inhibits the growth of malignant breast tumors and their associated metastases.[1][2] Its anticancer effects may be due to silencing the GSTP1 gene.[3]

Some piperlongumine derivatives were potent anti-inflammatory agents.[4] The synthesis typically involved Schotten-Baumann reaction between the acid chloride of 3,4,5-trimethoxycinnamic acid with the corresponding amines. Wang et al., evaluated piperlongumine as a novel senolytic agent.[5]

References[edit]

  1. ^ a b c Raj, Lakshmi; Ide, Takao; Gurkar, Aditi U.; Foley, Michael; Schenone, Monica; Li, Xiaoyu; Tolliday, Nicola J.; Golub, Todd R.; et al. (2011). "Selective killing of cancer cells by a small molecule targeting the stress response to ROS". Nature. 475 (7355): 231–234. PMC 3316487Freely accessible. PMID 21753854. doi:10.1038/nature10167. 
  2. ^ "Novel Compound Selectively Kills Cancer Cells by Blocking Their Response to Oxidative Stress". ScienceDaily. July 2011. 
  3. ^ Researchers uncover mechanism for cancer-killing properties of pepper plant reporting on Structural and Biochemical Analyses Reveal the Mechanism of Glutathione S-Transferase Pi 1 Inhibition by the Anti-cancer Compound Piperlongumine. 2017
  4. ^ Seo, Young Hwa; Kim, Jin-Kyung; Jun, Jong-Gab (2014). "Synthesis and biological evaluation of piperlongumine derivatives as potent anti-inflammatory agents". Bioorganic & Medicinal Chemistry Letters. 24 (24): 5727–5730. ISSN 0960-894X. PMID 25453809. doi:10.1016/j.bmcl.2014.10.054. 
  5. ^ Wang, Y.; Chang, J.; Liu, X.; Zhang, X.; Zhang, S.; Zhang, X.; Zheng, G. (2016). "Discovery of piperlongumine as a potential novel lead for the development of senolytic agents". Aging. 8 (11): 2915–2926. doi:10.18632/aging.101100. 

External links[edit]