Kavalactone

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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 the kava shrub.

Contents

[edit] Compounds

See also: Flavokavain

At least 18 different kavalactones have been identified to date, with methysticin being the first identified.[1] Synthetic analogues, such as ethysticin, also exist.[2]

Kavalactones
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
5,6-dehydrokavain 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 - - -H -H
Methysticin 7 - - -H -H
7,8-dihydromethysticin 8 - - -H -H
Kavalactones: General structures
Structure 1
Structure 2
Structure 3
Structure 4
Structure 5
Structure 6
Structure 7
Structure 8

[edit] See also

[edit] References

  1. ^ Naumov, P., Dragull, K., Yoshioka, M., Tang, C.-S.; Ng, S. W. "Structural Characterization of Genuine (—)-Pipermethystine, (—)-Epoxypipermethystine, (+)-Dihydromethysticin and Yangonin from the Kava Plant (Piper methysticum)", Natural Product Communications(2008), 3(8) 1333—1336.
  2. ^ Shulgin, A (1973). "The narcotic ppper - the chemistry and pharmacology of Piper methysticum and related species". Bull. Narc. 25 (59): 59–74. 

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