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Desmethoxyyangonin

5,6-Dehydrokavain 4-Methoxy-6-[(E)-2-phenylvinyl]-2-pyranone

Desmethoxyyangonin or 5,6-dehydrokavain is one of the six main kavalactones found in the Piper methysticum (kava) plant. It is a reversible inhibitor of monoamine oxidase B (MAO-B), likely contributing to increased dopamine levels in the brain’s nucleus accumbens and supporting kava’s attention-enhancing effects. Unlike other kavalactones, it does not modulate GABAA receptors. It also strongly induces the liver enzyme CYP3A23. It is an active compound in Alpinia pricei with anti-inflammatory and liver-protective effects that improve survival in mice with endotoxin-induced hepatitis.

Pharmacology

Desmethoxyyangonin is a reversible inhibitor of monoamine oxidase B (MAO-B). Kava is able to increase dopamine levels in the nucleus accumbens and desmethoxyyangonin likely contributes to this effect. This, along with several other catecholamines, may be responsible for the purported attention-promoting effects of kava.

Unlike the other major kavalactones, desmethoxyyangonin does not appear to act as a GABAA receptor positive allosteric modulator.

Desmethoxyyangonin has marked activity on the induction of CYP3A23.

It is an active compound in the Formosan plant Alpinia pricei and exhibits potent anti-inflammatory and hepatoprotective effects by inhibiting immune cell activation and key inflammatory signaling pathways, significantly improving survival and metabolic balance in mice with endotoxin-induced fulminant hepatitis.

References

References

  1. Uebelhack, R. (September 1998). "Inhibition of platelet MAO-B by kava pyrone-enriched extract from Piper methysticum Forster (kava-kava)". Pharmacopsychiatry.
  2. Baum, SS. (October 1998). "Effect of kava extract and individual kavapyrones on neurotransmitter levels in the nucleus accumbens of rats". Progress in Neuro-Psychopharmacology and Biological Psychiatry.
  3. (1998). "Influence of genuine kavapyrone enantiomers on the GABA-A binding site". Planta Medica.
  4. Ma, Yuzhong. (November 2004). "Desmethoxyyangonin and dihydromethysticin are two major pharmacological kavalactones with marked activity on the induction of CYP3A23". Drug Metabolism and Disposition.
  5. Chou T-W, Feng J-H, Huang C-C, Cheng Y-W, Chien S-C, Wang S-Y, et al. (2013) A Plant Kavalactone Desmethoxyyangonin Prevents Inflammation and Fulminant Hepatitis in Mice. PLoS ONE 8(10): e77626. doi:10.1371/journal.pone.0077626
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monoamine-oxidase-inhibitors kavalactones alkene-derivatives ethers nootropics
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