| Identification | Back Directory | [Name]
WEDELOLACTONE | [CAS]
524-12-9 | [Synonyms]
Wedelolactone
Wedelia lactone
Wedelolactone CRS
Wedelolactone, ≥98%(HPLC)
IKK Inhibitor II, Wedelolactone
5,11,12-Trihydroxy-7-MethoxycouMestan
Wedelolactone, 98%, from Wedelia chinensis (Osbeck.) Merr.
1,8,9-trihydroxy-3-Methoxy-6H-benzofuro[3,2-c]chroMen-6-one
IKK Inhibitor II, Wedelolactone - CAS 524-12-9 - Calbiochem
1,8,9-trihydroxy-3-methoxy-[1]benzofuro[3,2-c]chromen-6-one
1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c][1]benzopyran-6-one
6H-Benzofuro(3,2-C)(1)benzopyran-6-one, 1,8,9-trihydroxy-3-methoxy- | [EINECS(EC#)]
200-158-5 | [Molecular Formula]
C16H10O7 | [MDL Number]
MFCD07778564 | [MOL File]
524-12-9.mol | [Molecular Weight]
314.25 |
| Chemical Properties | Back Directory | [Melting point ]
327～330℃ | [Boiling point ]
498.4±45.0 °C(Predicted) | [density ]
1.655±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
DMSO: 14 mg/mL, soluble
| [form ]
solid
| [pka]
6.90±0.20(Predicted) | [color ]
brown-beige
| [InChI]
InChI=1S/C16H10O7/c1-21-6-2-10(19)14-12(3-6)23-16(20)13-7-4-8(17)9(18)5-11(7)22-15(13)14/h2-5,17-19H,1H3 | [InChIKey]
XQDCKJKKMFWXGB-UHFFFAOYSA-N | [SMILES]
C1(=O)OC2=CC(OC)=CC(O)=C2C2OC3=CC(O)=C(O)C=C3C1=2 |
| Hazard Information | Back Directory | [Chemical Properties]
Soluble in methanol, DMSO and other solvents, insoluble in petroleum ether, dichloromethane and chloroform. Derived from the above-ground part of the Asteraceae plant Eclipta prostrasta L. | [Uses]
Wedelolactone is a naturally occuring furanocoumarin isolated from Eclipta prostrata, an herbal medicine used to treat septic shock in traditional Chinese medicine. It inhibits the IκB kinase (IKK) complex and supresses LPS-induced caspase-11 expression in LPS-treated BALB 3T3 cells (IC50=35μM) | [Definition]
ChEBI: A member of the class of coumestans that is coumestan with hydroxy substituents as positions 1, 8 and 9 and a methoxy substituent at position 3. | [Biological Activity]
wedelolactone is an inhibitor of ikk.ikb kinase (ikk) complex contains the catalytic subunits ikkα and ikkβ, and the regulatory subunit ikkγ/nemo. ikk, is a kinase critical for activation of nf-κb by mediating phosphorylation and degradation of iκbα. the induction of caspase-11 is an important upstream controlling event in inflammatory response and apoptosis under pathological conditions modulated by upstream nf-κb-mediated transcription[1]. | [Biochem/physiol Actions]
Wedelolactone inhibits NF-κB-mediated gene transcription in cells by blocking the phosphorylation and degradation of IκBα. Irreversible inhibitor of IKKα and β kinase activity (IC50 < 10 μM). Wedelolactone has no effects on p38 MAP kinase or Akt. | [in vitro]
in cultured mouse balb/c 3t3 cells, mouse splenocytes and hela cells, wedelolactone (0~100 μm) inhibited lps-induced caspase-11 expression by inhibiting nf-κb-mediated transcription through the direct inhibition of ikk. wedelolactone played an potential role in anti-inflammatory therapy to inhibit il-1β levels in diseases such as rheumatoid arthritis, asthma and septic shock[1]. | [in vivo]
on swiss albino male mouse skin, ikk inhibition by wedelolactone (10 μm) prevented the induction of nf-κb, perturbed the generation of reactive oxygen species and reactive nitrogen intermediates, blunted the signal transduction that lead to the activation of the early immediate genes, and thereby protected mouse skin from the uvb induced neoplastic transformation, angiotropism and metastatic progression [2]. | [storage]
Store at 2-8°C | [References]
[1] kobori m, yang z, gong d, et al. wedelolactone suppresses lps-induced caspase-11 expression by directly inhibiting the ikk complex.[j]. cell death & differentiation, 2004, 11(1):123-30.
[2] ali f, khan b a, sultana s. wedelolactone mitigates uvb induced oxidative stress, inflammation and early tumor promotion events in murine skin: plausible role of nfκb pathway[j]. european journal of pharmacology, 2016, 786:253-264. |
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