wedelolactone

Names

[ CAS No. ]:
524-12-9

[ Name ]:
wedelolactone

[Synonym ]:
6H-Benzofuro[3,2-c][1]benzopyran-6-one, 1,8,9-trihydroxy-3-methoxy-
wedelolactone
1,8,9-Trihydroxy-3-methoxy-6H-[1]benzofuro[3,2-c]chromen-6-one
6H-Benzofuro(3,2-c)(1)benzopyran-6-one, 1,8,9-trihydroxy-3-methoxy-
1,8,9-trihydroxy-3-methoxycoumestan

Biological Activity

[Description]:

Wedelolactone, a natural product from Ecliptae herba, suppresses LPS-induced caspase-11 expression by directly inhibiting the IKK Complex[1]. Wedelolactone inhibits 5-lipoxygenase (5-Lox) (IC50~2.5 μM) activity by an oxygen radical scavenging mechanism. Wedelolactone induces caspase-dependent apoptosis in prostate cancer cells via downregulation of PKCε without inhibiting Akt[2]. Anti-cancer, anti-inflammatory, and antioxidant activities[3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Signaling Pathways >> Apoptosis >> Caspase

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Metabolic Enzyme/Protease >> 5-Lipoxygenase

[Target]

Caspase-11

5-lipoxygenase:2.5 μM (IC50)

Apoptosis

[References]

[1]. Kobori M, et al. Wedelolactone suppresses LPS-induced caspase-11 expression by directly inhibiting the IKK complex. Cell Death Differ. 2004 Jan;11(1):123-30.

[2]. Sarveswaran S, et al. Wedelolactone, a medicinal plant-derived coumestan, induces caspase-dependent apoptosis in prostate cancer cells via downregulation of PKCε without inhibiting Akt. Int J Oncol. 2012 Dec;41(6):2191-9.

[3]. Liu YQ, et al. Wedelolactone enhances osteoblastogenesis by regulating Wnt/β-catenin signaling pathway but suppresses osteoclastogenesis by NF-κB/c-fos/NFATc1 pathway. Sci Rep. 2016 Aug 25;6:32260.

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Boiling Point ]:
498.4±45.0 °C at 760 mmHg

[ Melting Point ]:
315 °C

[ Molecular Formula ]:
C₁₆H₁₀O₇

[ Molecular Weight ]:
314.246

[ Flash Point ]:
255.2±28.7 °C

[ Exact Mass ]:
314.042664

[ PSA ]:
113.27000

[ LogP ]:
2.75

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.759

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
DMSO: 14 mg/mL, soluble

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H317

[ Precautionary Statements ]:
P280-P301 + P312 + P330

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R22;R43

[ Safety Phrases ]:
36/37

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2932999099

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Understanding the mechanisms controlling Leishmania amazonensis infection in vitro: the role of LTB4 derived from human neutrophils.

J. Infect. Dis. 210(4) , 656-66, (2014)

Neutrophils are rapidly recruited to the site of Leishmania infection and play an active role in capturing and killing parasites. They are the main source of leukotriene B4 (LTB4), a potent proinflamm...

CYLD is a crucial negative regulator of innate immune response in Escherichia coli pneumonia.

Cell. Microbiol. 10(11) , 2247-56, (2008)

Bacteraemic pneumonia is a common cause of sepsis in critically ill patients today and is characterized by dysregulation of inflammation. The genetic factors predisposing to bacteraemic pneumonia are ...

Demethylwedelolactone derivatives inhibit invasive growth in vitro and lung metastasis of MDA-MB-231 breast cancer cells in nude mice.

Eur. J. Med. Chem. 56 , 361-7, (2012)

The anticancer properties of demethylwedelolactone (DWEL) and wedelolactone (WEL), which are naturally occurring coumestans, have not been well characterized. In this study, we investigated the anti-i...

Related Compounds

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