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Kavalactones

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File:Kavalactone-general-numbered.svg

Kavalactones are a class of lactone compounds found in the kava shrub. Kavalactones have a wide variety of effects including amnestic, analgesic, anticonvulsant, anxiolytic, nootropic, and sedative/hypnotic activity caused by numerous interactions with the central nervous system via a myriad of mechanisms.

Enzyme inhibitionEdit

Kava extract has been shown to potently inhibit a wide range of hepatic enzymes, suggesting a very high potential for interactions with many pharmaceuticals and herbal medications.[1] For this reason, kava should never be consumed without the permission of your primary care physician, psychiatrist, and/or any other doctor who is prescribing medication for you. It is also recommended that you discuss your kava use with your pharmacist. Inform your anesthesiologist of your kava use well in advance of any surgery, you may be instructed to temporarily discontinue your kava use for a set period of time before and after the surgery.

ToxicityEdit

Several kavalactones (e.g. Flavokavain B, Methysticin and Yangonin) have been reported to be toxic and/or carcinogenic, although further research into these mechanisms is needed and it is not yet known if kava consumption induces toxic/carcinogenic effects in vivo. Despite this, hepatoxicity has been reported in a small portion of previously healthy kava users.[2][3]

Numerous kavalactones have apoptotic effects on various human tissues, which may be involved in some of the purported toxic effects of kava use.[4][5][6]

Compounds Edit

See also: Flavokavain

At least 18 different kavalactones have been identified to date, with methysticin being the first identified.[7]

Multiple analogues, such as ethysticin, have also been isolated.[8]

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

Template:General kavalactone structures

See alsoEdit

ReferencesEdit

  1. James M. Mathews, Amy S. Etheridge and Sherry R. Black. Inhibition of Human Cytochrome P450 Activities by Kava Extract and Kavalactones.
  2. Dr Joji Malani (2002). Evaluation of the effects of Kava on the Liver. (PDF) URL accessed on 2008-01-05.
  3. AC Brown (2007). Traditional kava beverage consumption and liver function tests in a predominantly Tongan population in Hawaii revealed no liver impairment.. URL accessed on 2009-03-17.
  4. (2010). Kavalactones Yangonin and Methysticin Induce Apoptosis in Human Hepatocytes (HepG2) In Vitro.. Phytotherapy research : PTR 25 (3): n/a.
  5. Zi X, Simoneau AR. Flavokawain A, a novel chalcone from kava extract, induces apoptosis in bladder cancer cells by involvement of Bax protein-dependent and mitochondria-dependent apoptotic pathway and suppresses tumor growth in mice.. Cancer Research.
  6. Ramez N. Eskander1, Leslie M. Randall1, Toshinori Sakai, Yi Guy, Bang Hoang, Xiaolin Zi. Flavokawain B, a novel, naturally occurring chalcone, exhibits robust apoptotic effects and induces G2/M arrest of a uterine leiomyosarcoma cell line.
  7. (2008). Structural Characterization of Genuine (-)-Pipermethystine, (-)-Epoxypipermethystine, (+)-Dihydromethysticin and Yangonin from the Kava Plant (Piper methysticum). Natural Product Communications 3 (8): 1333–1336.
  8. Shulgin, A. (1973). The narcotic pepper - the chemistry and pharmacology of Piper methysticum and related species. Bulletin on Narcotics (2): 59–74.

External linksEdit

Template:Kava

Template:Natural phenol

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