YANGONIN Chemical Properties

Melting point:

155-157°

Boiling point:

487.6±45.0 °C(Predicted)

Density 

1.325 g/cm3

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

color 

Pale Yellow to Pale Green

BRN 

230710

Stability:

Light Sensitive

LogP

1.750 (est)

Safety Information

WGK Germany 

3

YANGONIN Usage And Synthesis

Uses

A lactone isolated from the Kava plant (Piper methysticum). The active constituents of Kava are a group of approx. 18 compounds collectively referred to as kavalactones or kava pyrones. Kawain, dihydrokawain, methysticin, dihydromethysticin, yangonin, and desmethoxyyangonin are the six major kavalactones. Kava beverages and other preparations are known to be anxiolytic and are used for anxiety disorders. Dietary supplements containing the root of the kava shrub have been implicated in several cases of liver toxicity in humans, including several who required liver transplants after using kava supplements.

Description

Yangonin is a natural kavalactone from the kava plant, P. methysticum. It enhances the binding of bicuculline at the γ-amino butyric acid (GABA) receptor GABA_A at 1.0 μM. Yangonin also binds the central cannabinoid (CB₁) receptor with a K_i value of 0.72 μM, but whether it serves as an agonist or antagonist at this receptor remains to be determined. Yangonin blocks the activation of NF-κB by TNF-α. It also inhibits anchorage-dependent and independent growth of bladder cancer cell lines through induction of autophagic cell death (IC₅₀s = 15-59 mg/mL).

Chemical Properties

It is soluble in organic solvents such as methanol, ethanol, and DMSO. It is derived from the root of Piper methysticum Forst.

Uses

A lactone isolated from the Kava plant (Piper methysticum). The active constituents of Kava are a group of approx. 18 compounds collectively referred to as kavalactones or kava pyrones. Kawain, dihydrokawain, methysticin, dihydromethysticin, yangonin, and desmethoxyyangonin are the six major kavalactones. Kava beverages and other preparations are known to be anxiolytic and are used for anxiety disorders. Dietary supplements containing the root of the kava shrub have been implicated in several cases of liver toxicity in humans, including several who required liver transplants after using kava supplements.

Uses

A lactone isolated from the Kava plant (Piper methysticum). rokawain, methysticin, dihydromethysticin, yangonin, and desmethoxyyangonin are the six major kavalactones. Kava beverages and other preparations are known to be anxiolytic and are used for anxiety d isorders. a supplements.

Definition

ChEBI: Yangonin is a member of 2-pyranones and an aromatic ether.

IC 50

CB1: 1.79 μM (IC₅₀); CB1: 0.72 μM (Ki); RelA

References

[1] ALESSIA LIGRESTI . Kavalactones and the endocannabinoid system: The plant-derived yangonin is a novel CB1 receptor ligand[J]. Pharmacological research, 2012, 66 2: Pages 163-169. DOI: 10.1016/j.phrs.2012.04.003
[2] G BOONEN  H H. Influence of genuine kavapyrone enantiomers on the GABA-A binding site.[J]. Planta medica, 1998, 64 6: 504-506. DOI: 10.1055/s-2006-957502
[3] JUAN MA . Yangonin Blocks Tumor Necrosis Factor-α–Induced Nuclear Factor-κB–Dependent Transcription by Inhibiting the Transactivation Potential of the RelA/p65 Subunit[J]. Journal of pharmacological sciences, 2012, 118 4: Pages 447-454. DOI: 10.1254/jphs.11215fp
[4] ZHONGBO LIU. Kavalactone yangonin induces autophagy and sensitizes bladder cancer cells to flavokawain A and docetaxel via inhibition of the mTOR pathway.[J]. Journal of Biomedical Research, 2017, 31 5: 408-418. DOI: 10.7555/jbr.31.20160160

YANGONIN(500-62-9)Related Product Information

• L-KAWAIN
• FLAVOKAVAIN A(P)
• DIHYDROMETHYSTICIN
• Dihydrokawain
• 4',6'-DIMETHOXY-2'-HYDROXYCHALCONE
• METHYSTICIN
• FLAVOKAWAINC
• Kavain
• YANGONIN(P),YANGONIN SNAP-N-SHOOT 0.1mg/mL(P)
• YANGONIN(PRIMARY STANDARD)
• 2-ACETOXY-1,3-BUTADIENE
• 4-Methoxy-6-methyl-2H-pyran-2-one
• DIHYDROKAVAIN
• DEHYDROMETHYSTICIN
• YANGONIN