Yangonin

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Yangonin
Yangonin.svg
Yangonin02.png
Names
IUPAC name
4-Methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]pyran-2-one
Identifiers
500-62-9 YesY
ChEMBL ChEMBL1098658 N
ChemSpider 4444896 N
Jmol-3D images Image
PubChem 5281575
UNII R970U49V3C N
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).
 N verify (what isYesY/N?)
Infobox references

Yangonin is one of the six major kavalactones found in the kava plant.[1] It has been shown to possess significant binding affinity for the cannabinoid receptor CB1, where it behaves as an agonist.[2] As a result, yangonin may be responsible for some of kava's intoxicating effects.

Medical use[edit]

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.[citation needed]

Toxicity[edit]

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[edit]

  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 ofPiper 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.