Yangonin

Yangonin

Names
IUPAC name 4-Methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]pyran-2-one
Identifiers
CAS Number	500-62-9
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL1098658
ChemSpider	4444896
ECHA InfoCard	100.211.821
PubChem	5281575
UNII	R970U49V3C
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	258.27 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 (K_i = 0.72 μM), where it behaves as an agonist.^[2]

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 : PTR. 25 (3): n/a. doi:10.1002/ptr.3283. PMID 20734326.