Desmethoxyyangonin

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 GABA_A 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.

Desmethoxyyangonin

Names
Preferred IUPAC name 4-Methoxy-6-[(E)-2-phenylethen-1-yl]-2H-pyran-2-one
Other names (E)-4-Methoxy-6-styryl-2H-pyran-2-one 5,6-Dehydrokavain 4-Methoxy-6-[(E)-2-phenylvinyl]-2-pyranone
Identifiers
CAS Number	15345-89-8 Y
3D model (JSmol)	Interactive image Interactive image
ChEMBL	ChEMBL254218 Y
ChemSpider	4438012 Y
PubChem CID	5273621
UNII	F2MBQ8QRUN Y
CompTox Dashboard (EPA)	DTXSID4033390
InChI InChI=1S/C14H12O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-10H,1H3/b8-7+ Y Key: DKKJNZYHGRUXBS-BQYQJAHWSA-N Y InChI=1/C14H12O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-10H,1H3/b8-7+ Key: DKKJNZYHGRUXBS-BQYQJAHWBF
SMILES COC1=CC(=O)OC(=C1)C=CC2=CC=CC=C2 O=C/1O\C(=CC(\OC)=C\1)\C=C\c2ccccc2
Properties
Chemical formula	C14H12O3
Molar mass	228.247 g·mol−1
Appearance	white to faint yellow powder
Density	1.18 g/mL
Melting point	148 °C (298 °F; 421 K)
Boiling point	440 °C (824 °F; 713 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Pharmacology

Desmethoxyyangonin is a reversible inhibitor of monoamine oxidase B (MAO-B).^[1] Kava is able to increase dopamine levels in the nucleus accumbens^[2] 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 GABA_A receptor positive allosteric modulator.^[3]

Desmethoxyyangonin has marked activity on the induction of CYP3A23.^[4]

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.^[5]

See also

• Kavain