Yangonin

Yangonin

Names
IUPAC name 4-Methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]pyran-2-one
Identifiers
CAS Number	500-62-9
ChEMBL	ChEMBL1098658
ChemSpider	4444896
Jmol 3D model	Interactive image
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).
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), where it behaves as an agonist.^[2] As a result, yangonin may be responsible for some of kava's intoxicating effects.

Biological effects

The CB₁ activity of yangonin likely contributes to its psychoactive effects. This, along with the GABAergic effects of other kavalactones has given kava a use in the ethnobotanical treatment of anxiety, insomnia, pain, and other disorders.^[3][4] However, anxiety relief is unlikely to be contributed to yangonin's CB₁ agonistic properties as CB₁ agonism can be anxiogenic rather than anxiolytic.

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.^[5]

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. Feltenstein, M. W.; Lambdin, L. C.; Ganzera, M.; Ranjith, H.; Dharmaratne, W.; Nanayakkara, N. P. D.; Khan, I. A.; Sufka, K. J. (2003). "Anxiolytic properties of Piper methysticumextract samples and fractions in the chick social-separation-stress procedure". Phytotherapy Research 17 (3): 210–216. doi:10.1002/ptr.1107. PMID 12672148.
4. "Kava : MedicinePlus".
5. 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.