PIPERLONGUMINE

PIPERLONGUMINE Basic information
Product Name:PIPERLONGUMINE
Synonyms:PIPERLONGUMIN;PIPERLONGUMINE;PIPLARTINE;5,6-DIHYDRO-1-[1-OXO-3-3,4,5-TRIMETHOXYPHENYL-TRANS-2-PROPENYL]-21H-PYRIDINONE;piperlongumine from long pepper;(E)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one;PPLGM;1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one
CAS:20069-09-4
MF:C17H19NO5
MW:317.34
EINECS:
Product Categories:Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:20069-09-4.mol
PIPERLONGUMINE Structure
PIPERLONGUMINE Chemical Properties
Melting point 124°C
Boiling point 475.6±45.0 °C(Predicted)
density 1.223±0.06 g/cm3(Predicted)
storage temp. 2-8°C
solubility DMSO: ≥5mg/mL at warmed to 60°C
pka-1.88±0.20(Predicted)
form powder
color white to beige
Stability:Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
LogP2.340 (est)
Safety Information
WGK Germany 3
RTECS UU7785850
HS Code 2932209090
MSDS Information
ProviderLanguage
SigmaAldrich English
PIPERLONGUMINE Usage And Synthesis
DescriptionA piperidinone alkaloid present in Piper longum, the structure has been shown to be N-(3:4:5-trimethoxycinnamoyl)-Lls-piperidin-2-one. In the plant, the base occurs mainly in the roots.
UsesPiperlongumine has been used to study the regulation of protein regulator of cytokinesis 1 (PRC1) expression. It has also been used to investigate its anti-tumor effects on human melanoma cells in vitro.
UsesPiperlongumine (PL), a new alkaloid abundantly present in Piper longum fruits strongly inhibited platelet cell aggregation. It may have anti-cancer properties. It selectively targets and kills cancer cells but leaving normal cells unharmed.
Usesanti-asthma, antibronchitis
DefinitionChEBI: Piplartine is a member of cinnamamides and a dicarboximide.
General DescriptionPiperlongumine is an alkaloid, which is extracted from Piper longum Linn. It exhibits anti-atherosclerotic, anxiolytic, antidiabetic, antidepressant, antibacterial, anti-platelet, aggregation, anxiolytic and anti-inflammatory properties. Piperlongumine prevents the production of tumor necrosis factor-α and interleukin-6. It blocks the activation of nuclear factor-κB (NF-κB) against proinflammatory responses. Piperlongumine inhibits plaque formation and inhibits vascular smooth muscle cell migration. It is used to treat cough, respiratory infections and stomach-ache.
Biochem/physiol ActionsPiperlongumine selectively kills cancer cells regardless of p53 status without harming normal cells. It binds to and inihbits proteins known to regulate oxidative stress, in particular, Glutathione S-transferase pi 1 (GSTP1). It increases the level of reactive oxygen species (ROS) and apoptotic cell death in cancer cells with little effect on either rapidly or slowly dividing primary normal cells. Piperlongumine showed significant antitumour effects in a variety of mouse tumour models and inhibited growth of spontaneously formed malignant breast tumours and their associated metastases.
targetP450 (e.g. CYP17) | Antifection
ReferencesChatterjee, Dutta., Tetrahedron, 23, 1769 (1967)
PIPERLONGUMINE Preparation Products And Raw materials
Daurinoline VERATRIDINE Xanthiside 2-[2-(Methylamino)benzoyl]-3,4-dihydro-β-carboline-1(2H)-one menisdaurin 3,4,5-TRIMETHOXYCINNAMALDEHYDE PIPERLONGUMINE(RG) SINAPINALDEHYDE N-ALLYLACRYLAMIDE 1-METHYL-1,2,3,6-TETRAHYDROPYRIDINE CHEMBRDG-BB 9071121 CHEMBRDG-BB 9070763 CINNAMAMIDE, N-ALLYL-, (E)- N,N-DIETHYLACRYLAMIDE 5-PROPENYL-1,2,3-TRIMETHOXY PIPERLONGUMINE Cintramide 4-HYDROXY-3-METHOXYCINNAMIDE

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