| Identification | Back Directory | [Name]
YANGONIN | [CAS]
500-62-9 | [Synonyms]
Yan
Y100550
YANGONIN
11-METHOXYYANGONIN
Yangoninpproved, it should be
Yangonin, 98%, from Piper methysticum Forst
4-methoxy-6-(p-methoxystyryl)-2h-pyran-2-on
4-methoxy-6-(p-methoxystyryl)-2h-pyran-2-one
4-Methoxy-6-((E)-4-methoxystyryl)pyran-2-one
4-methoxy-6-(beta-(p-anisyl)vinyl)-alpha-pyrone
(E)-4-Methoxy-6-(4-methoxystyryl)-2H-pyran-2-one
4-Methoxy-6-[2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one
4-Methoxy-6-[(E)-2-(4-methoxyphenyl)vinyl]-2H-pyran-2-one
2H-Pyran-2-one, 4-methoxy-6-[(1E)-2-(4-methoxyphenyl)ethenyl]-
5-hydroxy-3-methoxy-7-(p-methoxyphenyl)-2,4,6-heptatrienoicacidgamma-lacton | [Molecular Formula]
C15H14O4 | [MDL Number]
MFCD00221733 | [MOL File]
500-62-9.mol | [Molecular Weight]
258.27 |
| Questions And Answer | Back Directory | [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. |
| Chemical Properties | Back Directory | [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 ]
neat | [color ]
Pale Yellow to Pale Green | [BRN ]
230710 | [Stability:]
Light Sensitive | [LogP]
1.750 (est) |
| Hazard Information | Back Directory | [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 GABAA at 1.0 μM.1 Yangonin also binds the central cannabinoid (CB1) receptor with a Ki value of 0.72 μM, but whether it serves as an agonist or antagonist at this receptor remains to be determined.2 Yangonin blocks the activation of NF-κB by TNF-α.3 It also inhibits anchorage-dependent and independent growth of bladder cancer cell lines through induction of autophagic cell death (IC50s = 15-59 mg/mL).4 | [Chemical Properties]
It is soluble in organic solvents such as methanol, ethanol, and DMSO. It is derived from the root of Piper methysticum Forst. | [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 |
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