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Yangonin

Names
Preferred IUPAC name 4-Methoxy-6--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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is  ?) Infobox references

Yangonin is one of the six major kavalactones found in the kava plant. 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.

Like other kavalactones, yangonin has been found to potentiate GABA_A receptors. 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, 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.

Biosynthesis

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

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. "Yangonin".
4. ^ 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.

• Kavalactones
• 4-Methoxyphenyl compounds
• Analgesics
• CB1 receptor agonists
• GABAA receptor positive allosteric modulators
• Monoamine oxidase inhibitors