Piperlonguminine
Piperlonguminine is found in several species of the Piper plant and displays many beneficial characteristics, including antithrombotic, anti-inflammatory, anti-hyperlipidemic, antibacterial, anti-parasitic, antifungal, neuroprotective, and anticancer chemotherapeutic activities. In animal models, piperlonguminine inhibits generation of factor Xa and thrombin and production of TNF-α-induced plasminogen activator inhibitor type 1 (PAI-1), increasing bleeding time. This compound decreases PMA-stimulated phosphorylation or activation of NF-κB, p38, ERK1/2, and JNK and also decreases levels of IL-6 and TNF-α. In other animal studies, piperlonguminine increases LDL receptor mRNA and decreases total serum cholesterol (including an increase in HDL and decreases in LDL and triglyceride levels). Piperlonguminine also promotes adipogenesis, increasing mRNA levels of adiponectin, glutamate transporter 4 (GLUT4), fatty acid binding protein aP2, and PPARγ in vitro. This compound displays cytotoxicity against gram-positive bacteria (Bacillus), parasites (Trypanosoma cruzi), and fungus (Candida). Piperlonguminine decreases levels of amyloid-B (Aβ) and amyloid precursor protein (APP) in vitro, suggesting potential benefit in the treatment of Alzheimer’s disease. Additionally, piperlonguminine decreases tumor growth in animal models.
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/18954701
| Cas No. |
5950-12-9 |
|---|---|
| Purity |
≥99% |
| Formula |
C16H19NO3 |
| Formula Wt. |
273.33 |
| Chemical Name |
(2E, 4E)-5-Benzo[d][1,3]-dioxol-5-yl)-N-isobutylpenta-2,4-dienamide |
| IUPAC Name |
(2E,4E)-5-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)penta-2,4-dienamide |
| Melting Point |
168-169°C |
| Solubility |
DMSO |
| Appearance |
White to off white powder |
Lee W, Yoo H, Ku SK, et al. Anticoagulant activities of piperlonguminine in vitro and in vivo. BMB Rep. 2013 Oct;46(10):484-9. PMID: 24148768.
Ku SK, Kim JA, Bae JS. Piperlonguminine Downregulates Endothelial Protein C Receptor Shedding In Vitro and In Vivo. Inflammation. 2013 Oct 15. [Epub ahead of print]. PMID: 24127121.
Lee W, Yoo H, Kim JA, et al. Barrier protective effects of piperlonguminine in LPS-induced inflammation in vitro and in vivo. Food Chem Toxicol. 2013 Aug;58:149-57. PMID: 23619565.
Yamaguchi I, Matsuda H, Zhang H, et al. Adipogenic effects of piperlonguminine in 3T3-L1 cells and plasma concentrations of several amide constituents from Piper chaba extracts after treatment of mice. J Nat Med. 2013 Apr 13. [Epub ahead of print]. PMID: 23584920.
Bao L, Borjihan G. Hypolipidemic effects of piperlonguminine in HepG2 cells and in Wistar rats. Pharmazie. 2012 Oct;67(10):858-61. PMID: 23136721.
Qi HS, Liu P, Gao SQ, et al. Inhibitory effect of piperlonguminine/ dihydropiperlonguminine on the production of amyloid beta and APP in SK-N-SH cells. Chin J Physiol. 2009 Jun 30;52(3):160-8. PMID: 19777802.
Silva DR, Endo EH, Filho BP, et al. Chemical Composition and Antimicrobial Properties of Piper ovatum Vahl. Molecules. 2009 Mar 16;14(3):1171-82. PMID: 19325517
Bezerra DP, Pessoa C, Moraes MO, et al. In vivo growth inhibition of sarcoma 180 by piperlonguminine, an alkaloid amide from the Piper species. J Appl Toxicol. 2008 Jul;28(5):599-607. PMID: 17975786.
