Yangonin

Yangonin
Names
Preferred IUPAC name
4-Methoxy-6-[(E)-2-(4-methoxyphenyl)ethen-1-yl]-2H-pyran-2-one
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.211.821
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PubChem CID
UNII
InChI
  • InChI=1S/C15H14O4/c1-17-12-6-3-11(4-7-12)5-8-13-9-14(18-2)10-15(16)19-13/h3-10H,1-2H3/b8-5+ ☒N
    Key: XLHIYUYCSMZCCC-VMPITWQZSA-N ☒N
  • InChI=1/C15H14O4/c1-17-12-6-3-11(4-7-12)5-8-13-9-14(18-2)10-15(16)19-13/h3-10H,1-2H3/b8-5+
    Key: XLHIYUYCSMZCCC-VMPITWQZBG
SMILES
  • COC1=CC=C(C=C1)/C=C/C2=CC(=CC(=O)O2)OC
Properties
Chemical formula
 C15H14O4
Molar mass 258.273 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Yangonin is one of the six major kavalactones found in the kava plant.[1] It has been shown to possess binding affinity for the cannabinoid receptor CB1 (Ki = 0.72 μM), and selectivity vs. the CB₂ receptor (K(i)>10 μM) where it behaves as an agonist. The CB₁ receptor affinity of yangonin suggests that the endocannabinoid system might contribute to the complex human psychopharmacology of the traditional kava drink and the anxiolytic preparations obtained from the kava plant.[2]

Further in vitro studies have also demonstrated yangonin to be a clinically significant inhibitor of monoamine oxidase, with a moderate preference for isozyme B, which could open the door to a wide range of interactions.


Toxicity

Yangonin displays marked in vitro toxicity on human hepatocytes with approximately 40% reduction in viability based on an ethidium bromide assay. The predominant mode of cell death turned out to be apoptosis rather than necrosis. No significant changes were observed in glutathione levels.[3]

References

  1. ↑ Malani, Joji (2002-12-03). "Evaluation of the effects of Kava on the Liver" (PDF). Fiji School of Medicine. Retrieved 2009-09-04.
  2. ↑ Ligresti, A.; Villano, R.; Allarà, M.; Ujváry, I. N.; Di Marzo, V. (2012). "Kavalactones and the endocannabinoid system: The plant-derived yangonin is a novel CB1 receptor ligand". Pharmacological Research. 66 (2): 163–169. doi:10.1016/j.phrs.2012.04.003. PMID 22525682.
  3. ↑ Tang, J; Dunlop, RA; Rowe, A; Rodgers, KJ; Ramzan, I (2010). "Kavalactones Yangonin and Methysticin Induce Apoptosis in Human Hepatocytes (HepG2) In Vitro". Phytotherapy Research. 25 (3): 417–23. doi:10.1002/ptr.3283. PMID 20734326. S2CID 19717477.
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