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'''Piperlongumine''' (also called '''piplartine''' or '''piperlongumin''') is an ] ] constituent<ref name="pubchem">{{cite web |title=Piperlongumine |url=https://pubchem.ncbi.nlm.nih.gov/compound/Piperlongumine |publisher=PubChem, US National Library of Medicine |access-date=5 December 2020 |date=29 November 2020}}</ref> of the fruit of the ] (''Piper longum''), a pepper plant found in ] and ].<ref name="piska">{{cite journal | last=Piska | first=Kamil | last2=Gunia-Krzyżak | first2=Agnieszka | last3=Koczurkiewicz | first3=Paulina | last4=Wójcik-Pszczoła | first4=Katarzyna | last5=Pękala | first5=Elżbieta | title=Piperlongumine (piplartine) as a lead compound for anticancer agents – Synthesis and properties of analogues: A mini-review | journal=European Journal of Medicinal Chemistry| volume=156 | year=2018 | issn=0223-5234 | doi=10.1016/j.ejmech.2018.06.057 | pages=13–20|pmid=30006159}}</ref> When ]ed, piperlongumine may cause skin, eye or ] irritation.<ref name=pubchem/> '''Piperlongumine''' (also called '''piplartine''' or '''piperlongumin''') is an ] ] constituent<ref name="pubchem">{{cite web |title=Piperlongumine |url=https://pubchem.ncbi.nlm.nih.gov/compound/Piperlongumine |publisher=PubChem, US National Library of Medicine |access-date=5 December 2020 |date=29 November 2020}}</ref> of the fruit of the ] (''Piper longum''), a pepper plant found in ] and ].<ref name="piska">{{cite journal | last1=Piska | first1=Kamil | last2=Gunia-Krzyżak | first2=Agnieszka | last3=Koczurkiewicz | first3=Paulina | last4=Wójcik-Pszczoła | first4=Katarzyna | last5=Pękala | first5=Elżbieta | title=Piperlongumine (piplartine) as a lead compound for anticancer agents – Synthesis and properties of analogues: A mini-review | journal=European Journal of Medicinal Chemistry| volume=156 | year=2018 | issn=0223-5234 | doi=10.1016/j.ejmech.2018.06.057 | pages=13–20|pmid=30006159}}</ref> When ]ed, piperlongumine may cause skin, eye or ] irritation.<ref name=pubchem/>


==Traditional medicine and research== ==Traditional medicine and research==

Revision as of 16:27, 27 September 2023

Piperlongumine
Names
Preferred IUPAC name 1--5,6-dihydropyridin-2(1H)-one
Other names Piplartine
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.243.690 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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+Key: VABYUUZNAVQNPG-BQYQJAHWSA-N
SMILES
  • O=C2\C=C/CCN2C(=O)\C=C\c1cc(OC)c(OC)c(OC)c1
Properties
Chemical formula C17H19NO5
Molar mass 317.341 g·mol
Solubility DMSO, DMF, ethanol
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements P261, P264, P280
Safety data sheet (SDS)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Piperlongumine (also called piplartine or piperlongumin) is an amide alkaloid constituent of the fruit of the long pepper (Piper longum), a pepper plant found in southern India and southeast Asia. When extracted, piperlongumine may cause skin, eye or respiratory tract irritation.

Traditional medicine and research

Long peppers have been used in Ayurveda and traditional Chinese medicine as a treatment.

Targtex, a biotechnology spin-off of the Portuguese Institute for Molecular Biology, developed a piperlongumine hydrogel that is to be applied after the removal of Glioblastoma tumours, with the goal of neutralizing remaining cancer cells. The hydrogel was effective in laboratory and animal studies and is scheduled for Phase I human clinical trials sometime in 2023.

References

  1. ^ "Safety Data Sheet Piperlongumine" (PDF). chemblink.com. October 1, 2018. Retrieved April 4, 2022.
  2. ^ "Piperlongumine". PubChem, US National Library of Medicine. 29 November 2020. Retrieved 5 December 2020.
  3. ^ Piska, Kamil; Gunia-Krzyżak, Agnieszka; Koczurkiewicz, Paulina; Wójcik-Pszczoła, Katarzyna; Pękala, Elżbieta (2018). "Piperlongumine (piplartine) as a lead compound for anticancer agents – Synthesis and properties of analogues: A mini-review". European Journal of Medicinal Chemistry. 156: 13–20. doi:10.1016/j.ejmech.2018.06.057. ISSN 0223-5234. PMID 30006159.
  4. "Piperlongumine". US National Center for Advancing Translational Sciences. 2020. Retrieved 5 December 2020.
  5. "Research & Technology | TargTex". Retrieved 2022-02-11.
  6. Renascença (2022-02-11). "Português cria hidrogel de pimenta para combater cancro do cérebro - Renascença". Rádio Renascença (in European Portuguese). Retrieved 2022-02-11.
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