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Yangonin

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Yangonin
Names
Preferred IUPAC name
4-Methoxy-6-[(E)-2-(4-methoxyphenyl)ethen-1-yl]-2H-pyran-2-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.211.821 Edit this at Wikidata
UNII
  • 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+ ☒N
    Key: XLHIYUYCSMZCCC-VMPITWQZSA-N ☒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
  • COC1=CC=C(C=C1)/C=C/C2=CC(=CC(=O)O2)OC
Properties
C15H14O4
Molar mass 258.273 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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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), and selectivity vs. the CB2 receptor (Ki >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.[2]

Further in vitro studies have also demonstrated yangonin to be an inhibitor of monoamine oxidase,[citation needed] 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.[3] The predominant mode of cell death turned out to be apoptosis rather than necrosis. No significant changes were observed in glutathione levels.[3]

Biosynthesis

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

Biosynthesis of yangonin. SAM = S-adenosyl methionine

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. ^ a b 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.
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