Yangonin

Names

[ CAS No. ]:
500-62-9

[ Name ]:
Yangonin

[Synonym ]:
4-Methoxy-6-[(E)-2-(4-methoxyphenyl)vinyl]-2H-pyran-2-one
5-Hydroxy-3-methoxy-7-(p-methoxyphenyl)-2,4,6-heptatrienoic Acid d-Lactone
4-Méthoxy-6-[(E)-2-(4-méthoxyphényl)éthènyl]-2H-pyran-2-one
2H-Pyran-2-one, 4-methoxy-6-[2-(4-methoxyphenyl)ethenyl]-, (E)-
2H-Pyran-2-one, 4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]-
4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one
4-Methoxy-6-((E)-4-methoxystyryl)pyran-2-one
4-Methoxy-6-[b-(p-anisyl)vinyl]-a-pyrone
6-(p-Methoxystyryl)-4-methoxy-a-pyrone
Yangonin
(E)-4-Methoxy-6-[2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one

Biological Activity

[Description]:

Yangonin exhibits affinity for the human recombinant cannabinoid CB1 receptor with an IC50 and a Ki of 1.79 ± 0.53 μM and 0.72±0.21 μM, respectively.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Cannabinoid Receptor

Research Areas >> Inflammation/Immunology

Natural Products >> Others

[Target]

CB1 Receptor:1.79 μM (IC50)

CB1 Receptor:0.72 μM (Ki)

RelA

[In Vitro]

Yangonin is one of the six major kavalactones found in Piper methysticum.Yangonin potently inhibits NF-κB activation through suppression of the transcriptional activity of the RelA/p65 subunit of NF-κB. Yangonin significantly inhibits the induced expression of the NF-κB-reporter gene. However, Yangonin does not interfere with TNF-α-induced inhibitor of κBα (IκBα) degradation, p65 nuclear translocation, and DNA-binding activity of NF-κB. Yangonin inhibits not only the induced NF-κB activation by overexpression of RelA/p65, but also transactivation activity of RelA/p65. Yangonin does not inhibit TNF-α-induced activation of p38, but it significantly impairs activation of ERK 1/2 and stress-activated protein kinase/JNK[2].

[Cell Assay]

HeLa cells are seeded at 1×105 cells/mL in 96-well plates containing 100 μL of DMEM medium with 10% FBS and incubated overnight. Yangonin is dissolved in DMSO and DMSO is added to all plates to compensate the same volume of DMSO. After 24 h, the cells are pretreated with different concentrations of Yangonin (0.1-3 μM) for 1 h, followed by stimulation with or without TNF-α for 24 h. Subsequently, cells are cultured with MTT solution (5 mg/mL) for 3 h. The viable cells convert MTT to formazan, which generates a blue-purple color after dissolving in 150 μL of DMSO. The absorbance at 570 nm is measured by an ELISA plate reader[2].

[References]

[1]. Ligresti A, et al. Kavalactones and the endocannabinoid system: the plant-derived yangonin is a novel CB₁ receptor ligand. Pharmacol Res. 2012 Aug;66(2):163-9.

[2]. Ma J, et al. Yangonin blocks tumor necrosis factor-α-induced nuclear factor-κB-dependent transcription by inhibiting the transactivation potential of the RelA/p65 subunit. J Pharmacol Sci. 2012;118(4):447-54.

[3]. Wruck CJ, et al. Kavalactones protect neural cells against amyloid beta peptide-induced neurotoxicity via extracellular signal-regulated kinase 1/2-dependent nuclear factor erythroid 2-related factor 2 activation. Mol Pharmacol. 2008 Jun;73(6):1785-95.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
487.6±45.0 °C at 760 mmHg

[ Melting Point ]:
155-157ºC

[ Molecular Formula ]:
C₁₅H₁₄O₄

[ Molecular Weight ]:
258.269

[ Flash Point ]:
219.7±28.8 °C

[ Exact Mass ]:
258.089203

[ PSA ]:
48.67000

[ LogP ]:
1.75

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.578

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UQ1225200

CHEMICAL NAME :: 2H-Pyran-2-one, 4-methoxy-6-(p-methoxystyryl)-

CAS REGISTRY NUMBER :: 500-62-9

LAST UPDATED :: 199109

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C15-H14-O4

MOLECULAR WEIGHT :: 258.29

WISWESSER LINE NOTATION :: T6OVJ DO1 F1U1R DO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >1500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 177,261,1969

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >1500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 177,261,1969

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 41 mg/kg

TOXIC EFFECTS :: Behavioral - anticonvulsant

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 177,261,1969

Safety Information

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2932999099

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%

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In recent years, Kava kava (Piper methysticum, Forst. f., Piperaceae), a folkloric beverage and popular herbal remedy, has been implicated in a number of liver failure cases. Many hypotheses as to the...

Related Compounds

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