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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
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Medicinal and ethnoveterinary remedies of hunters in Trinidad.
2001
Synthesis and preliminary pharmacological evaluation of coumestans with different patterns of oxygenation.
2001 Feb 12
[Studies on the chemical constituents of Eclipta prostrata (L)].
2001 Jan
Trypsin inhibitory effect of wedelolactone and demethylwedelolactone.
2003 Apr
Optimization of wedelolactone accumulation in shoot cultures of Eclipta alba.
2003 Dec
Total synthesis of wedelolactone.
2003 Oct 31
Preliminary immunomodulatory activities of methanol extracts of Eclipta alba and Centella asiatica.
2004
Wedelolactone suppresses LPS-induced caspase-11 expression by directly inhibiting the IKK complex.
2004 Jan
Structure-activity relationship of wedelolactone analogues: structural requirements for inhibition of Na+, K+ -ATPase and binding to the central benzodiazepine receptor.
2006 Dec 1
Activity of Wedelia calendulacea Less. in post-menopausal osteoporosis.
2006 Jan
Compounds from Wedelia chinensis synergistically suppress androgen activity and growth in prostate cancer cells.
2007 Dec
Leishmania promastigotes activate PI3K/Akt signalling to confer host cell resistance to apoptosis.
2007 Jan
The onset of labor alters corticotropin-releasing hormone type 1 receptor variant expression in human myometrium: putative role of interleukin-1beta.
2007 Jul
[Simultaneous determination of wedelolactone and isodemethylwedelolactone in Herba ecliptae by reversed-phase high performance liquid chromatography].
2007 May
HIV-1 protease and HIV-1 integrase inhibitory substances from Eclipta prostrata.
2007 Nov
Action of fibroblast growth factor-2 on the intervertebral disc.
2008
Cell type-specific activation of the cytomegalovirus promoter by dimethylsulfoxide and 5-aza-2'-deoxycytidine.
2008
Targeted delivery of a designed sTRAIL mutant results in superior apoptotic activity towards EGFR-positive tumor cells.
2008 Aug
Hair growth promoting activity of Eclipta alba in male albino rats.
2008 Aug
Lipid-soluble smoke particles upregulate vascular smooth muscle ETB receptors via activation of mitogen-activating protein kinases and NF-kappaB pathways.
2008 Dec
Non-nucleoside inhibitors of the hepatitis C virus NS5B RNA-dependant RNA polymerase: 2-aryl-3-heteroaryl-1,3-thiazolidin-4-one derivatives.
2008 Dec 1
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
Inhibition of NFkappaB reduces cellular viability in GH3 pituitary adenoma cells.
2008 May
CYLD is a crucial negative regulator of innate immune response in Escherichia coli pneumonia.
2008 Nov
Simultaneous inhibition of the constitutively activated nuclear factor kappaB and of the interleukin-6 pathways is necessary and sufficient to completely overcome apoptosis resistance of human U266 myeloma cells.
2008 Oct
Simultaneous estimation of andrographolide and wedelolactone in herbal formulations.
2008 Sep
Stimulation of iNOS expression and apoptosis resistance in B-cell chronic lymphocytic leukemia (B-CLL) cells through engagement of Toll-like receptor 7 (TLR-7) and NF-kappaB activation.
2008 Sep
Inhibition of snake venoms and phospholipases A(2) by extracts from native and genetically modified Eclipta alba: isolation of active coumestans.
2009 Apr
Pharmacologic inhibitors of IkappaB kinase suppress growth and migration of mammary carcinosarcoma cells in vitro and prevent osteolytic bone metastasis in vivo.
2009 Aug
High glucose-induced IKK-Hsp-90 interaction contributes to endothelial dysfunction.
2009 Jan
Discovery of a potent and selective inhibitor for human carbonyl reductase 1 from propionate scanning applied to the macrolide zearalenone.
2009 Jan 15
Mechanisms of interleukin-1beta-induced GDNF release from rat glioma cells.
2009 Jun 5
Herbal extract of Wedelia chinensis attenuates androgen receptor activity and orthotopic growth of prostate cancer in nude mice.
2009 Sep 1
Modulation of the BRCA1 Protein and Induction of Apoptosis in Triple Negative Breast Cancer Cell Lines by the Polyphenolic Compound Curcumin.
2009 Sep 2
Ability of a synthetic coumestan to antagonize Bothrops snake venom activities.
2010 Feb-Mar
[Regulation of NF-κB signal transduction pathway on cytokines in cultured nasal epithelium].
2010 Jul
Mechanisms of tumor necrosis factor-alpha-induced interleukin-6 synthesis in glioma cells.
2010 Mar 6
p53-mediated delayed NF-κB activity enhances etoposide-induced cell death in medulloblastoma.
2010 May 13
Inflammatory responses in epithelia: endotoxin-induced IL-6 secretion and iNOS/NO production are differentially regulated in mouse mammary epithelial cells.
2010 Nov 30
Cigarette smoke extract promotes human vascular smooth muscle cell proliferation and survival through ERK1/2- and NF-κB-dependent pathways.
2010 Nov 4
Heparin at low concentration acts as antivenom against Bothrops jararacussu venom and bothropstoxin-I neurotoxic and myotoxic actions.
2010 Oct 15
Lipid soluble smoke particles upregulate endothelin receptors in rat basilar artery.
2010 Sep 1
Redox state alters anti-cancer effects of wedelolactone.
2012 Aug
Activation of nuclear factor-κB pathway is responsible for tumor necrosis factor-α-induced up-regulation of endothelin B2 receptor expression in vascular smooth muscle cells in vitro.
2012 Mar 7
TNF-α-mediated NF-κB survival signaling impairment by cisplatin enhances JNK activation allowing synergistic apoptosis of renal proximal tubular cells.
2013 Jan 15
Palmitate-induced endothelial dysfunction is attenuated by cyanidin-3-O-glucoside through modulation of Nrf2/Bach1 and NF-κB pathways.
2015 Dec 15
15-Oxoeicosatetraenoic acid is a 15-hydroxyprostaglandin dehydrogenase-derived electrophilic mediator of inflammatory signaling pathways.
2015 Jun 5
Caspase-11 plays an essential role in methamphetamine-induced dopaminergic neuron apoptosis.
2015 May
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
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
Created
by admin
on Fri Dec 15 19:50:25 UTC 2023
Edited
by admin
on Fri Dec 15 19:50:25 UTC 2023
Record UNII
0K6L725GNS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
WEDELOLACTONE
Common Name English
1,8,9-TRIHYDROXY-3-METHOXY-6H-(1)BENZOFURO(3,2-C)CHROMEN-6-ONE
Systematic Name English
7-METHOXY-5,11,12-TRIHYDROXYCOUMESTAN
Common Name English
Code System Code Type Description
WIKIPEDIA
WEDELOLACTONE
Created by admin on Fri Dec 15 19:50:25 UTC 2023 , Edited by admin on Fri Dec 15 19:50:25 UTC 2023
PRIMARY
EPA CompTox
DTXSID60200408
Created by admin on Fri Dec 15 19:50:25 UTC 2023 , Edited by admin on Fri Dec 15 19:50:25 UTC 2023
PRIMARY
PUBCHEM
5281813
Created by admin on Fri Dec 15 19:50:25 UTC 2023 , Edited by admin on Fri Dec 15 19:50:25 UTC 2023
PRIMARY
CHEBI
10037
Created by admin on Fri Dec 15 19:50:25 UTC 2023 , Edited by admin on Fri Dec 15 19:50:25 UTC 2023
PRIMARY
CAS
524-12-9
Created by admin on Fri Dec 15 19:50:25 UTC 2023 , Edited by admin on Fri Dec 15 19:50:25 UTC 2023
PRIMARY
FDA UNII
0K6L725GNS
Created by admin on Fri Dec 15 19:50:25 UTC 2023 , Edited by admin on Fri Dec 15 19:50:25 UTC 2023
PRIMARY