5950-12-9
Chemical Structure
Piperlonguminine
- CAS No.: 5950-12-9
- Formula:C16H19NO3
- Molecular Weight:273.33
IUPAC Name: (2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)-N-isobutylpenta-2,4-dienamide
InChIKey: WHAAPCGHVWVUEX-GGWOSOGESA-N
SMILES: O=C(NCC(C)C)/C=C/C=C/C1=CC=C(OCO2)C2=C1
Biological Activity:
Piperlonguminine is a cytochrome P450 (CYP450) inhibitor. Piperlonguminine also inhibits the growth of epimastigotes and intracellular amastigotes of Trypanosoma cruzi, with IC50 values of 53.8 and 33.9 μM, respectively[10]. Piperlonguminine regulates HMGB1/TLR4-NF-κB/MAPK-related inflammatory responses, endothelial protein C receptor (EPCR) shedding, melanogenesis, glycolipid metabolism, ischemic brain injury and tumor growth. Piperlonguminine can be used in research on hyperlipidemia, sepsis, Chagas disease, ischemic stroke, sarcoma and severe acute pancreatitis-associated lung injury[1][2][3][4][5][6][7][8][9][10][11][12].
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Piperlonguminine | 99.81% | Piperlonguminine is a cytochrome P450 (CYP450) inhibitor. Piperlonguminine also inhibits the growth of epimastigotes and intracellular amastigotes of Trypanosoma cruzi, with IC50 values of 53.8 and 33.9 μM, respectively. Piperlonguminine regulates HMGB1/TLR4-NF-κB/MAPK-related inflammatory responses, endothelial protein C receptor (EPCR) shedding, melanogenesis, glycolipid metabolism, ischemic brain injury and tumor growth. Piperlonguminine can be used in research on hyperlipidemia, sepsis, Chagas disease, ischemic stroke, sarcoma and severe acute pancreatitis-associated lung injury. |
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Piperlonguminine (Standard) | ≥98% | Piperlonguminine (Standard) is the analytical standard of Piperlonguminine (HY-126562). This product is intended for research and analytical applications. Piperlonguminine is a cytochrome P450 (CYP450) inhibitor. Piperlonguminine also inhibits the growth of epimastigotes and intracellular amastigotes of Trypanosoma cruzi, with IC50 values of 53.8 and 33.9 μM, respectively. Piperlonguminine regulates HMGB1/TLR4-NF-κB/MAPK-related inflammatory responses, endothelial protein C receptor (EPCR) shedding, melanogenesis, glycolipid metabolism, ischemic brain injury and tumor growth. Piperlonguminine can be used in research on hyperlipidemia, sepsis, Chagas disease, ischemic stroke, sarcoma and severe acute pancreatitis-associated lung injury. |
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References
- [1]. Wang H, et al. Protection effect of piperine and piperlonguminine from Piper longum L. alkaloids against rotenone-induced neuronal injury. Brain research. 2016 May 15;1639:214-27.
- [2]. Ku SK, et al. Vascular barrier protective effects of piperlonguminine in vitro and in vivo. Inflammation research : official journal of the European Histamine Research Society ... [et al.]. 2014 May;63(5):369-79.
- [3]. Sarnaizul E, et al. The preparation and antihyperlipidaemic assay of piperlonguminine in vivo. Phytochemistry Letters. 2012, article in press.
- [4]. Bezerra DP, et al. In vivo growth inhibition of sarcoma 180 by piperlonguminine, an alkaloid amide from the Piper species. Journal of applied toxicology : JAT. 2008 Jul;28(5):599-607. [Content Brief]
- [5]. Lee W, et al. Barrier protective effects of piperlonguminine in LPS-induced inflammation in vitro and in vivo. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2013 Aug;58:149-57.
- [6]. Chi Y, et al. Metabolic activation and cytochrome P450 inhibition of piperlonguminine mediated by CYP3A4. International journal of biological macromolecules. 2024 May;268(Pt 2):131502.
- [7]. Ku SK, et al. Piperlonguminine downregulates endothelial protein C receptor shedding in vitro and in vivo. Inflammation. 2014 Apr;37(2):435-42.
- [8]. Yamaguchi I, 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. Journal of Natural Medicines. 2013.
- [9]. Kim KS, et al. Inhibitory effect of piperlonguminine on melanin production in melanoma B16 cell line by downregulation of tyrosinase expression. Pigment cell research. 2006 Feb;19(1):90-8.
- [10]. Veiga-Santos P, et al. The natural compounds piperovatine and piperlonguminine induce autophagic cell death on Trypanosoma cruzi. Acta tropica. 2013 Mar;125(3):349-56.
- [11]. Yang T, et al. Piperlonguminine is neuroprotective in experimental rat stroke. International immunopharmacology. 2014 Dec;23(2):447-51. [Content Brief]
- [12]. Hu Q, et al. Effects of piperlonguminine on lung injury in severe acute pancreatitis via the TLR4/NF-κB pathway. European journal of histochemistry : EJH. 2023 Mar 20;67(2):3639. [Content Brief]
