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

form 

powder

pka

-1.88±0.20(Predicted)

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.

LogP

2.340 (est)

Safety Information

WGK Germany 

3

RTECS 

UU7785850

HS Code 

2932209090

MSDS

• Language:English Provider:SigmaAldrich

PIPERLONGUMINE Usage And Synthesis

Description

A 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.

Uses

Piperlongumine 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.

Uses

anti-asthma, antibronchitis

Uses

Piperlongumine (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.

Definition

ChEBI: Piplartine is a member of cinnamamides and a dicarboximide.

General Description

Piperlongumine 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 Actions

Piperlongumine 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.

target

P450 (e.g. CYP17) | Antifection

References

Chatterjee, Dutta., Tetrahedron, 23, 1769 (1967)

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