| Identification | Back Directory | [Name]
Parthenolide | [CAS]
20554-84-1 | [Synonyms]
PTL
Nsc157035
Aids007764
Parthelide
Aids-007764
Parthenolide
PartheNAlide
Parthenolides
Parthenolide(PTL)
Parthenolide (25 mg)
Parthenolide ((-)-Parthenolide)
PARTHENOLIDE, TANACETUM PARTHENIUM
Parthenolide from Chrysanthenum parthenium
Oxireno(9,10)cyclodeca(1,2-B)furan-9(1ah)-o
Parthenolide, froM ChrysantheMuM MorifoliuM
Parthenolide, 98%, from Chrysanthemum morifolium
4,5α-Epoxy-6β-hydroxygermacra-1(10),11(13)-dien-12-oic acid γ-lactone
4,5-alpha-epoxy-6-beta-hydroxy-11(13)-dien-12-oicacigamma-germacra-1(10
4,5-alpha-epoxy-6-beta-hydroxygermacra-1(10),11(13)-dien-12-oicacidgamma-la
4,5alpha-epoxy-6beta-hydroxy-germacra-1(10),11(13)-dien-12-oic acid gamma-lactone
Germacra-1(10),11(13)-dien-12-oic acid, 4,5-alpha-epoxy-6-beta-hydroxy-, gamma-lactone
(1aR,4E,7aS,10aS,10bS)-2,3,6,7,7a,8,10a,10b-Octahydro-1a,5-dimethyl-8-methyleneoxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one
Oxireno9,10cyclodeca1,2-bfuran-9(1aH)-one, 2,3,6,7,7a,8,10a,10b-octahydro-1a,5-dimethyl-8-methylene-, (1aR,4E,7aS,10aS,10bR)-
Oxireno[9,10]cyclodeca[1,2-B]furan-9(1ah)-one, 2,3,6,7,7A,8,10A,10B-octahydro-1A,5-dimethyl-8-methylene-, (1ar,4E,7as,10as,10bs)-
(3aS,9aR,10aS,10bS,E)-6,9a-dimethyl-3-methylene-3a,4,5,8,9,9a,10a,10b-octahydrooxireno[2',3':9,10]cyclodeca[1,2-b]furan-2(3H)-one
[1AR-(1AR*,4E,7AS*,10AS*-10BR*)]-2,3-6,7,7A,8,10A,10B-OCTAHYDRO-1A,5-DIMETHYL-8-METHYLENEOXIRENO[9,10]CYCLODECA[1,2-B]FURAN-9(1AH)-ONE
[1aR-(1aR*,4E,7aS*,10aS*,-10bR*)]-2,3-6,7,7a,8,10a,10b-Octahydro-1a,5-dimethyl-8-methyleneoxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one | [EINECS(EC#)]
1592732-453-0 | [Molecular Formula]
C15H20O3 | [MDL Number]
MFCD00134592 | [MOL File]
20554-84-1.mol | [Molecular Weight]
248.32 |
| Chemical Properties | Back Directory | [Melting point ]
115-116 °C(lit.)
| [alpha ]
D20 -81.4° (c = 1.04 in chloroform); D22 -71.4° (c = 0.220 in CH2Cl2) | [Boiling point ]
394.1±42.0 °C(Predicted) | [density ]
1.13±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
Soluble in DMSO (up to 100 mg/ml) or in Ethanol (up to 20 mg/ml) | [form ]
White solid | [color ]
White | [Merck ]
14,7048 | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months. | [InChI]
InChI=1S/C15H20O3/c1-9-5-4-8-15(3)13(18-15)12-11(7-6-9)10(2)14(16)17-12/h5,11-13H,2,4,6-8H2,1,3H3/b9-5+/t11-,12-,13+,15+/m0/s1 | [Contact allergens]
Parthenolide is a sesquiterpene lactone found Asteraceae-
Compositae such as feverfew (Tanacetum parthenium
Schultz-Bip.) or congress grass (Parthenium hysterophorus
L.). | [InChIKey]
KTEXNACQROZXEV-PVLRGYAZSA-N | [SMILES]
O1C(=O)C(=C)[C@]2([H])CCC(C)=CCC[C@@]3(C)O[C@]3([H])[C@@]12[H] |t:10| | [LogP]
2.424 (est) | [CAS DataBase Reference]
20554-84-1 |
| Hazard Information | Back Directory | [Chemical Properties]
White solid | [Uses]
Antiinflammatory;MAP kinase inhibitor | [Definition]
ChEBI: A sesquiterpene lactone and active principle of Feverfew (Tanacetum parthenium). | [Uses]
Parthenolide is a sesquiterpene lactone from the plant feverfew (T. parthenium). It inhibits the growth of the promastigote form of L. amazonensis (IC50 = 3.6 μg/ml). Parthenolide also induces apoptosis in cancer cells, at least in part by inhibiting NF-κBand STAT-mediated anti-apoptotic gene transcription. This compound has also been shown to block inflammation by inhibiting signaling through NF-κB. Inhibition of NF-κB by parthenolide can be achieved by direct binding of the pattern recognition receptor NOD2 by parthenolide. | [Biological Activity]
The active principle of feverfew (Chrysanthemum parthenium), widely used as a herbal remedy for arthritis and migraine and as a febrifuge. Parthenolide is antisecretory, anti-inflammatory, spasmolytic and inhibits the release of 5-HT from blood platelets. Also inhibits generation of leukotriene B 4 and thromboxane B 2 . | [Description]
Parthenolide is an allergen in feverfew (Tanacetum
parthenarium). | [General Description]
This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG | [Biochem/physiol Actions]
Parthenolide is a sesquiterpene lactone present abundantly in the leaves and flowers of Tanacetum parthenium. It exhibits anti-cancer properties for the treatment of invasive cancers. Parthenolide exhibits therapeutic effects against inflammation and migraine. It plays a role in signal transduction and activation of transcription (STAT)-inhibition-mediated transcriptional repression of pro-apoptotic genes. | [Mechanism of action]
Parthenolide (PTL) is a potent NF-κB signaling inhibitor that exerts anti-inflammatory effects by inhibiting IκBα depletion, thereby inhibiting excessive NF-κB activation. It also inhibits the nuclear translocation of the p65 subunit and the DNA binding of the NF-κB complex to exert anti-tumor effects. In addition, it inhibits STAT and MAP kinase activity and induces sustained JNK activity and p53 activity by affecting MDM2 and HDAC1 levels, resulting in increased sensitivity of cancer cells to chemotherapy and radiotherapy. The most unique property is that it can induce cell death mainly in cancer cells while sparing healthy cells, and it also protects normal cells from UVB and oxidative stress. | [storage]
Store at -20°C | [References]
1) Kwok et al. (2001), The anti-inflammatory natural product parthenolide from the medicinal herb Feverfew directly binds to and inhibits IkappaB kinase; Chem. Biol., 8 759
2) Hwang et al. (1996), Inhibition of the expression of inducible cyclooxygenase and proinflammatory cytokines by sequiterpene lactones in macrophages correlates with the inhibition of MAP kinases; Biochem. Biophys. Res. Commun., 226 810
3) Barsby et al. (1992), Feverfew extracts and parthenolide irreversibly inhibit vascular responses of the rabbit aorta; J. Pharm. Pharmacol., 44 737
4) Sumner et al. (1992), Inhibition of 5-lipoxygenase and cyclo-oxygenase in leukocytes by feverfew. Involvement of sesquiterpene lactones and other components; Biochem. Pharmacol., 43 2313
5) Groenewegen et al. (1990), A comparison of the effects of an extract of feverfew and parthenolide, a component of feverfew, on human platelet activity in-vitro; J. Pharm. Pharmacol., 42 553 |
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