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AdipoGen Life Sciences
Piperlongumine
40
CHF
CHF 40.00
In stock
AG-CN2-0024-M01010 mgCHF 40.00
AG-CN2-0024-M05050 mgCHF 120.00
| Product Details | |
|---|---|
| Synonyms | Piplartine; 5,6-Dihydro-1-(1-oxo-3-[3,4,5-trimethoxyphenyl]-trans-2-propenyl)-2[1H]-pyridinone |
| Product Type | Chemical |
| Properties | |
| Formula |
C17H19NO5 |
| MW | 317.3 |
| CAS | 20069-09-4 |
| Source/Host Chemicals | Isolated from Piper longum roots. |
| Purity Chemicals | ≥97% |
| Appearance | White crystals. |
| Solubility | Soluble in DMSO, ethanol, methanol and dimethylformamide. |
| InChi Key | VABYUUZNAVQNPG-BQYQJAHWSA-N |
| Smiles | COC1=CC(\C=C\C(=O)N2CCC=CC2=O)=CC(OC)=C1OC |
| Shipping and Handling | |
| Shipping | AMBIENT |
| Short Term Storage | +4°C |
| Long Term Storage | -20°C |
| Use/Stability | Stable for at least 2 years after receipt when stored at -20°C. |
| Documents | |
| MSDS |
 Download PDF |
| Product Specification Sheet | |
| Datasheet |
Download PDF |
Description
- Cytotoxic against tumor cell lines [3, 4, 5].
- Induces necrosis and apoptosis in cancer cells [5, 9, 12].
- Shows anti-platelet aggregation activity possibly by inhibition of cyclooxgenase activity and a decrease in thromboxane A2 formation [4, 6, 10].
- Shows significant anxiolytic and antidepressant activities [7].
- Promotes adipogenesis of 3T3-L1 cells [8].
- Induces in vivo and in vitro mutagenicity in eukaryotic models [11].
- Selectively kills cancer cells by targeting the stress response to ROS [12].
- Shows in vitro schistosomicidal activity [13].
- Selective inhibitor of human immunoproteasome. Targets the β5i subunit (LMP7) (IC50=15µM) with minimal inhibition of human constitutive proteasome [14].
Product References
- Alkaloids of Piper longum Linn. I. Structure and synthesis of piperlongumine and piperlonguminine: A. Chatterjee & C.P Dutta; Tetrahedron 23, 1769 (1967)
- Cytotoxic pyridone alkaloids from the leaves of Piper aborescens: C.Y. Duh, et al.; J. Nat. Prod. 53, 1575 (1990)
- Antiproliferative effects of two amides, piperine and piplartine, from Piper species: D.P. Bezerra, et al.; Z. Naturforsch. C 60, 539 (2005)
- New cytotoxic cyclobutanoid amides, a new furanoid lignan and anti-platelet aggregation constituents from Piper arborescens: I.L. Tsai, et al.; Planta Med. 71, 535 (2005)
- Piplartine induces inhibition of leukemia cell proliferation triggering both apoptosis and necrosis pathways: D.P. Bezerra, et al.; Toxicol. In Vitro 21, 1 (2007)
- Piperlongumine, a constituent of Piper longum L., inhibits rabbit platelet aggregation as a thromboxane A(2) receptor antagonist: M. Iwashita, et al.; Eur. J. Pharmacol. 570, 38 (2007)
- Piplartine, an amide alkaloid from Piper tuberculatum, presents anxiolytic and antidepressant effects in mice: F.F. Cícero Bezerra, et al.; Phytomedicine 14, 605 (2007)
- Effects of amide constituents from pepper on adipogenesis in 3T3-L1 cells: H. Zhang, et al.; Bioorg. Med. Chem. Lett. 18, 3272 (2008)
- Piplartine induces caspase-mediated apoptosis in PC-3 human prostate cancer cells: E.H. Kong, et al.; Oncol. Rep. 20, 785 (2008)
- Antiplatelet effects of piplartine, an alkamide isolated from Piper tuberculatum: possible involvement of cyclooxygenase blockade and antioxidant activity: J.B. Fontenele, et al.; J. Pharm. Pharmacol. 61, 511 (2009)
- Piplartine induces genotoxicity in eukaryotic but not in prokaryotic model systems: D.P. Bezerra, et al.; Mutat. Res. 677, 8 (2009)
- Selective killing of cancer cells by a small molecule targeting the stress response to ROS: L. Raj, et al.; Nature 475, 231 (2011)
- Schistosoma mansoni: In vitro schistosomicidal activity of piplartine: J. Moraes, et al.; Exp. Parasitol. 127, 357 (2011)
- Piperlongumine and some of its analogs inhibit selectively the human immunoproteasome over the constitutive proteasome: E. Bosc, et al.; BBRC 496, 961 (2018)
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