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Kavalactone

Group of chemical compounds

The general structure of the kavalactones, without the R1-R2 -O-CH2-O- bridge and with all possible C=C double bonds shown.

Kavalactones are a class of lactone compounds found in kava roots and Alpinia zerumbet (shell ginger) and in several Gymnopilus, Phellinus and Inonotus fungi. Some kavalactones are bioactive. They are responsible for the psychoactive, analgesic, euphoric and sedative effects of kava.

Bioactivity

Kava extract interacts with many pharmaceuticals and herbal medications. In human volunteers, in vivo inhibition includes CYP1A2 and CYP2E1 through use of probe drugs to measure inhibition.

Research

Its anxiolytic and hepatotoxic properties have been investigated.

The major kavalactones (except for desmethoxyyangonin) potentiate GABAA receptors, which may underlie the anxiolytic and sedative properties of kava. Further, inhibition of the reuptake of norepinephrine and dopamine, binding to the CB1 receptor, inhibition of voltage-gated sodium and calcium channels, and monoamine oxidase B reversible inhibition are additional pharmacological actions that have been reported for kavalactones.

Toxicity

Several kavalactones (e.g., methysticin and yangonin) affect a group of enzymes involved in metabolism, called the CYP450 system. Hepatotoxicity occurred in a small portion of previously healthy kava users, particularly from extracts, as opposed to whole root powders.

Compounds

At least 18 different kavalactones are known, with methysticin being the first identified. | doi-access= free | url-access= subscription Multiple analogues, such as ethysticin, have also been isolated. Some consist of a substituted α-pyrone as the lactone, while others are partially saturated.

The average elimination half-life of kavalactones typically present in kava root is 9 hr.

Name	Structure	R1	R2	R3	R4
Yangonin	1	-OCH3	-H	-H	-H
10-methoxyyangonin	1	-OCH3	-H	-OCH3	-H
11-methoxyyangonin	1	-OCH3	-OCH3	-H	-H
11-hydroxyyangonin	1	-OCH3	-OH	-H	-H
Desmethoxyyangonin	1	-H	-H	-H	-H
11-methoxy-12-hydroxydehydrokavain	1	-OH	-OCH3	-H	-H
7,8-dihydroyangonin	2	-OCH3	-H	-H	-H
Kavain	3	-H	-H	-H	-H
5-hydroxykavain	3	-H	-H	-H	-OH
5,6-dihydroyangonin	3	-OCH3	-H	-H	-H
7,8-dihydrokavain	4	-H	-H	-H	-H
5,6,7,8-tetrahydroyangonin	4	-OCH3	-H	-H	-H
5,6-dehydromethysticin	5	-O-CH2-O-	-H	-H
Methysticin	7	-O-CH2-O-	-H	-H
7,8-dihydromethysticin	8	-O-CH2-O-	-H	-H

Kavalactones: General structures

Biosynthesis

The kavalactone biosynthetic pathway in Piper methysticum was described in 2019.

References

(2021). "A Review on Synthetic Approaches towards Kavalactones". Synthesis.
(1969). "Occurrence of bis-noryangonin in Gymnopilus spectabilis". Journal of Pharmaceutical Sciences.
(2022). "Kavalactones isolated from Alpinia zerumbet (Pers.) Burtt. Et Smith with protective effects against human umbilical vein endothelial cell damage induced by high glucose". Natural Product Research.
(2002). "Inhibition of Human Cytochrome P450 Activities by Kava Extract and Kavalactones". Drug Metabolism and Disposition.
(2005). "Traditional aqueous kava extracts inhibit cytochrome P450 1A2 in humans: Protective effect against environmental carcinogens?". [[Clinical Pharmacology & Therapeutics]].
(2005). "In vivo effects of goldenseal, kava kava, black cohosh, and valerian on human cytochrome P450 1A2, 2D6, 2E1, and 3A4/5 phenotypes". [[Clinical Pharmacology & Therapeutics]].
(2011-01-01). "Kava: A Comprehensive Review of Efficacy, Safety, and Psychopharmacology". Australian & New Zealand Journal of Psychiatry.
(2011). "Proposal for a kava quality standardization code". Food and Chemical Toxicology.
(2013). "Kavalactone content and chemotype of kava beverages prepared from roots and rhizomes of Isa and Mahakea varieties and extraction efficiency of kavalactones using different solvents". Journal of Food Science and Technology.
(2012). "Kavalactones and the endocannabinoid system: the plant-derived yangonin is a novel CB₁ receptor ligand". Pharmacol. Res..
(2002). "Therapeutic potential of kava in the treatment of anxiety disorders". CNS Drugs.
(2011). "Kava and kava hepatotoxicity: Requirements for novel experimental, ethnobotanical and clinical studies based on a review of the evidence". Phytotherapy Research.
(2010). "Kava (''Piper methysticum''): Pharmacodynamics/Kinetics". Sigma-Aldrich Co. LLC.
(2019-07-22). "The biosynthetic origin of psychoactive kavalactones in kava". Springer Science and Business Media LLC.

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monoamine-oxidase-inhibitors kavalactones gabaa-receptor-positive-allosteric-modulators anxiolytics analgesics sedatives anticonvulsants nootropics

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