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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 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1098658 ;
ChemSpider	4444896 ;
ECHA InfoCard	100.211.821
PubChem CID	5281575;
UNII	R970U49V3C ;
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+ Key: XLHIYUYCSMZCCC-VMPITWQZSA-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). verify (what is ?) 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.

References

^ Malani, Joji (2002-12-03). "Evaluation of the effects of Kava on the Liver" (PDF). Fiji School of Medicine. Retrieved 2009-09-04.
^ 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.
^ "Yangonin".
^ ^a ^b 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.