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Parthenolide

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Parthenolide Basic information

Product Name:
Parthenolide
Synonyms:
  • Parthenolide, Tanacetum parthenium - CAS 20554-84-1 - Calbiochem
  • Factory Price Parthenolide 20554-84-1
  • Natural Plant Extracts Parthenolide 20554-84-1 High Purity HPLC>98%
  • Feverfew P.E Parthenlide
  • [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,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
  • 4,5α-Epoxy-6β-hydroxygermacra-1(10),11(13)-dien-12-oic acid γ-lactone
  • 4,5alpha-epoxy-6beta-hydroxy-germacra-1(10),11(13)-dien-12-oic acid gamma-lactone
CAS:
20554-84-1
MF:
C15H20O3
MW:
248.32
EINECS:
692-532-0
Product Categories:
  • inhibitor
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
  • Sesqui-Terpenoids
  • Isoprenoid/terpenoidNeurotransmitters
  • Anti-Proliferative AgentsNutrition Research
  • Antitumor Agents
  • Biochemicals Found in Plants
  • Cancer Research
  • Others
  • Natural Product
  • Serotonergics
  • Prostanoid receptor and related
Mol File:
20554-84-1.mol
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Parthenolide Chemical Properties

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. 
-20°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
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
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Safety Information

Hazard Codes 
Xi,C,F
Risk Statements 
11-34
Safety Statements 
22-24/25-45-36/37/39-26-16
WGK Germany 
3
RTECS 
LY4220000
HS Code 
29322090

MSDS

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Parthenolide Usage And Synthesis

Description

(-)-Parthenolide (PTL) is a natural sesquiterpene lactone produced as a secondary metabolite by plants of the Asteraceae/ Compositae (daisies) and Magnoliaceae family (magnolias). It was first isolated from feverfew (Tanacetum parthenium L. Schulz Bip. or synonymously Chrysanthemum parthenium L. Bernh.). The plant owes its name to its use as a long known natural remedy for alleviating fever, migraine, rheumatoid arthritis, stomach ache, toothache, and insect bites, among other ailments. After it was shown that parthenolide is the main biologically active ingredient of these plant(s)1b, many studies have described promising anti-inflammatory and anti-tumour properties of the natural product. Interestingly, it was shown that PTL was cytotoxic to tumor cells while almost not affecting healthy cells at similar concentrations. Moreover, it was reported to be one of the few small molecules that selectively target cancer stem cells, which are still difficult to treat and a suspected reason for tumour relapse[6].

Chemical Properties

White solid

Uses

Antiinflammatory;MAP kinase inhibitor

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-κB- and 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.

Uses

Parthenolide is an anti-inflammatory agent used in the treatment of ischemic injury. Also acts as an anti-tumor and anti0leukemia agent targetting acute myeloid leukemia.

Definition

ChEBI: A sesquiterpene lactone and active principle of Feverfew (Tanacetum parthenium).

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

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 .

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.

Contact allergens

Parthenolide is a sesquiterpene lactone found Asteraceae- Compositae such as feverfew (Tanacetum parthenium Schultz-Bip.) or congress grass (Parthenium hysterophorus L.).

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
6) Freund, Robert R. A. et al. “Advances in chemistry and bioactivity of parthenolide?.” Natural Product Reports 4 (2019): 541–565.

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