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
PubChem CID	5281575
UNII	R970U49V3C N
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 verify (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]

Like other kavalactones, yangonin has been found to potentiate GABA_A receptors.^[3] This may contribute to the anxiolytic properties of yangonin and kava as a whole.

Further in vitro studies have also demonstrated yangonin to be an inhibitor of monoamine oxidase,^{[citation needed]} 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.^[4] The predominant mode of cell death turned out to be apoptosis rather than necrosis. No significant changes were observed in glutathione levels.^[4]

Biosynthesis

Yangonin is biosynthesized from coumaroyl-CoA and malonyl-CoA.

Biosynthesis of yangonin. SAM = S-adenosyl methionine

References

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