PIPERLONGUMINE

Synonym(s):5,6-Dihydro-1-(1-oxo-3-[3,4,5-trimethoxyphenyl]-trans-2-propenyl)-2[1H]-pyridinone;5,6-Dihydro-1-[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]-2(1H)-Pyridinone;Piplartin;Piplartine;Piplartine, (E)-1-(3-(3,4,5-Trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one

CAS NO.：20069-09-4
Empirical Formula: C17H19NO5
Molecular Weight: 317.34
MDL number: MFCD00075706
SAFETY DATA SHEET (SDS)
Update Date: 2024-10-29 11:48:30

What is PIPERLONGUMINE?

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.

The Uses of PIPERLONGUMINE

anti-asthma, antibronchitis

The Uses of PIPERLONGUMINE

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.

The Uses of PIPERLONGUMINE

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.

What are the applications of Application

Piperlongumine is a selective anticancer GSTP1 and Bcl-2 inhibitor

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.

References

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

Properties of PIPERLONGUMINE

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.

Safety information for PIPERLONGUMINE

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H302:Acute toxicity,oral H315:Skin corrosion/irritation H320:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.