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Details

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
Structure of WEDELOLACTONE

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

HIDE SMILES / InChI

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

Description

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

Targets

Primary TargetPharmacologyConditionPotency
10.0 µM [IC50]
2.5 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
Wedelolactone (40 and 80 uM) significantly inhibited NF-kB p65 DNA binding activity induced by LPS in BALBc cells. The addition of 50 and 100 uM wedelolactone inhibited the IL-1b secretion from primary mouse splenocytes in a dose-dependent manner.
Substance Class Chemical
Record UNII
0K6L725GNS
Record Status Validated (UNII)
Record Version