Desmethoxyyangonin
Chemical compound
From Wikipedia, the free encyclopedia
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 is an active compound in Alpinia pricei with anti-inflammatory and liver-protective effects that improve survival in mice with endotoxin-induced hepatitis.
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| Names | |
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| 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 | |
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3D model (JSmol) |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| 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).
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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 GABAA 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]