SML0221

Piperlongumine

≥97% (HPLC)

• 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
• Empirical Formula (Hill Notation): C₁₇H₁₉NO₅
• CAS Number: 20069-09-4
• Molecular Weight: 317.34
• MDL number: MFCD00075706
• UNSPSC Code: 51111800
• PubChem Substance ID: 329825240
• NACRES: NA.77

Properties

• Quality Level: 100
• assay: ≥97% (HPLC)
• form: powder
• color: white to beige
• solubility: DMSO: ≥5 mg/mL at warmed to 60 °C
• storage temp.: 2-8°C
• SMILES string: COc1cc(\C=C\C(=O)N2CCC=CC2=O)cc(OC)c1OC
• 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+
• InChI key: VABYUUZNAVQNPG-BQYQJAHWSA-N

Description

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.

Application

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.

Piperlongumine has been used:

• as a pro-oxidant drug to treat HepG2 cells expressing zinc finger protein (ZNF)32
• to test its anti-neuroinflammatory effects in BV2 microglial cells
• to test its inhibitory effect on human gastric cancer cell lines

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.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302
• pcodes: P264 - P270 - P301 + P312 - P501
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable