Piperlonguminine

SKU: orb1297237

Description

Piperlonguminine is a bioactive alkaloid amide from Piper species that acts as an Akt/mTOR signaling inhibitor. It induces autophagy and cell death, demonstrating antitumor and anti-inflammatory activities in both in vitro and in vivo cancer research models.

Research Area

Infectious Disease & Virology

Key Properties

• CAS Number: 5950-12-9
• MW: 273.33
• Purity: 99.91% (May vary between batches)
• Formula: C₁₆H₁₉NO₃
• SMILES: CC(C)CNC(=O)\C=C\C=C\c1ccc2OCOc2c1
• Target: Anti-infection|||Antifungal|||Antibacterial
• Solubility: DMSO:27.78 mg/mL (101.64 mM);10% DMSO+90% Corn Oil:1 mg/mL (3.66 mM)

Bioactivity

• In Vitro:
  Piperlonguminine from Piper longum was discovered to inhibit melanin production in melanoma B16 cells stimulated with alpha-melanocyte stimulating hormone (alpha-MSH), 3-isobutyl-1-methylxanthine or protoporphyrin IX, where the compound exhibited stronger depigmenting efficacy than kojic acid. However, piperlonguminine did not affect 1-oleoyl-2-acetyl-sn-glycerol-induced melanogenesis and did not affect protein kinase C-mediated melanin production. Surprisingly, piperlonguminine did not inhibit the catalytic activity of cell-free tyrosinase from melanoma B16 cells but rather suppressed tyrosinase mRNA expression. This effect was attributed to the inhibitory action of piperlonguminine on alpha-MSH-induced signaling through cAMP to the cAMP responsive element binding protein that in turn regulates the expression of the microphthalmia-associated transcription factor, a key activator of the tyrosinase promoter. This study demonstrates that piperlonguminine is an efficient depigmenting agent with a novel mechanism of action.
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Storage & Handling

• Storage: -20°C
• Expiration Date: 12 months from date of receipt.
• Disclaimer: For research use only

Alternative Names

alkaloid, anti-platelet, anti-melanogenic, antitumor, anti-inflammatory, Anti-infection, Antiinfection, Antifection, amide, antibacterial, antifungal, Bacterial, Fungal, neuroprotective, Inhibitor, inhibit, Piperlonguminine, Piper

Compound Identifiers

PubChem CID

5320621