Yangonin

Yangonin

Names
Preferred IUPAC name 4-Methoxy-6-[(E)-2-(4-methoxyphenyl)ethen-1-yl]-2H-pyran-2-one
Identifiers
CAS Number	500-62-9 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1098658 N
ChemSpider	4444896 N
ECHA InfoCard	100.211.821
PubChem CID	5281575
UNII	R970U49V3C N
CompTox Dashboard (EPA)	DTXSID4034102
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).
N  (what is YN ?)
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 (K_i = 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[]