Stereochemistry | ACHIRAL |
Molecular Formula | C16H10O7 |
Molecular Weight | 314.2464 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(O)=C2C3=C(C4=CC(O)=C(O)C=C4O3)C(=O)OC2=C1
InChI
InChIKey=XQDCKJKKMFWXGB-UHFFFAOYSA-N
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
Molecular Formula | C16H10O7 |
Molecular Weight | 314.2464 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Wedelolactone, a compound originally extracted from Eclipta alba, has been shown to inhibit caspase-11, which is a key regulator of proinflammatory cytokine IL-1β maturation and pathological apoptosis. Mechanistic studies suggest that caspase-11 is inhibited by reduction of NF-κB-mediated transcription. Furthermore, this compound has been shown to inhibit IKKγ, a kinase that is crucial for activation of NF-κB, as well as IKK α and IKK β. Weldelolactone also displays potent trypsin inhibition capacities. Additional studies suggest that Wedelolactone contains antagonistic properties towards two PLA2 myotoxins that were isolated from Agkistrodon contortix laticinctus and Crotalus virdis virdis. This agent has also been noted to contain antihepatotoxic behavior consequentially protecting primary cultured liver cells from the toxicity of CC14, Phalloidin, and galactosamine, and inhibit 5-lipoxygenase (5-LO) activity in porcine leukocytes. Wedelolactone was shown to act as anti-cancer agent for breast and prostate carcinomas in vitro and in vivo targeting multiple cellular proteins including androgen receptors, 5-lipoxygenase and topoisomerase IIα. It is cytotoxic to breast, prostate, pituitary and myeloma cancer cell lines in vitro at uM concentrations.
Originator
Approval Year
PubMed
Patents
Sample Use Guides
In a dextran sodium sulfate (DSS)-induced mouse model, oral administration of Wedelolactone (50mg/kg) significantly attenuated pathological colonic damage and inhibited inflammatory infiltration, myeloperoxidase and alkaline phosphatase activities through MAPKs and NF-κB signaling pathways, while activating AMPK in colons treated with DSS.
Route of Administration:
Oral