ChemicalBook CAS DataBase List 20069-09-4

20069-09-4

Name	PIPERLONGUMINE
CAS	20069-09-4
Molecular Formula	C17H19NO5
MDL Number	MFCD00075706
Molecular Weight	317.34
MOL File	20069-09-4.mol

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 Data

WGK Germany	3
RTECS	UU7785850
HS Code	2932209090

Hazard Information

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

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)

Spectrum Detail

Supplier

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