Yangonin

Yangonin
Names
IUPAC name
4-Methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]pyran-2-one
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.211.821
UNII
Properties
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 (Ki = 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. PMID 22525682. doi:10.1016/j.phrs.2012.04.003.
  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): 417–23. PMID 20734326. doi:10.1002/ptr.3283.
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