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
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
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 Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL1806 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22733624 |
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10.0 µM [IC50] | |||
Target ID: CHEMBL215 |
2.5 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Sources: https://www.ncbi.nlm.nih.gov/pubmed/28750357 |
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Medicinal and ethnoveterinary remedies of hunters in Trinidad. | 2001 |
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[Studies on the chemical constituents of Eclipta prostrata (L)]. | 2001 Jan |
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Trypsin inhibitory effect of wedelolactone and demethylwedelolactone. | 2003 Apr |
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Lipid-soluble smoke particles upregulate vascular smooth muscle ETB receptors via activation of mitogen-activating protein kinases and NF-kappaB pathways. | 2008 Dec |
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Two specific drugs, BMS-345541 and purvalanol A induce apoptosis of HTLV-1 infected cells through inhibition of the NF-kappaB and cell cycle pathways. | 2008 Jun 10 |
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Inhibition of NFkappaB reduces cellular viability in GH3 pituitary adenoma cells. | 2008 May |
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CYLD is a crucial negative regulator of innate immune response in Escherichia coli pneumonia. | 2008 Nov |
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Herbal extract of Wedelia chinensis attenuates androgen receptor activity and orthotopic growth of prostate cancer in nude mice. | 2009 Sep 1 |
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Ability of a synthetic coumestan to antagonize Bothrops snake venom activities. | 2010 Feb-Mar |
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[Regulation of NF-κB signal transduction pathway on cytokines in cultured nasal epithelium]. | 2010 Jul |
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p53-mediated delayed NF-κB activity enhances etoposide-induced cell death in medulloblastoma. | 2010 May 13 |
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Lipid soluble smoke particles upregulate endothelin receptors in rat basilar artery. | 2010 Sep 1 |
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TNF-α-mediated NF-κB survival signaling impairment by cisplatin enhances JNK activation allowing synergistic apoptosis of renal proximal tubular cells. | 2013 Jan 15 |
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15-Oxoeicosatetraenoic acid is a 15-hydroxyprostaglandin dehydrogenase-derived electrophilic mediator of inflammatory signaling pathways. | 2015 Jun 5 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28750357
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14526390
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.
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WEDELOLACTONE
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DTXSID60200408
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5281813
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10037
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524-12-9
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0K6L725GNS
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SUBSTANCE RECORD