Flavokavain B

Last updated
Flavokavain B
Flavokavain B.svg
Names
Preferred IUPAC name
2′-Hydroxy-4′,6′-dimethoxychalcone
Other names
Flavokawain B
Identifiers
3D model (JSmol)
2059845
PubChem CID
UNII
  • O=C(C2=C(O)C=C(OC)C=C2OC)/C=C/C1=CC=CC=C1
Properties
C17H16O4
Molar mass 284.311 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Flavokavain B is a flavokavain found in the kava plant. [1] In 2010 a paper was published identifying it as a glutathione-depleting hepatotoxin. [2]

Contents

FKB is said by enthusiasts to occur at higher concentrations in "tudei" kava strains, which are generally considered less desirable.

See also

Related Research Articles

Kava Species of plant

Kava or kava kava is a crop of the Pacific Islands. The name kava is from Tongan and Marquesan, meaning 'bitter'; other names for kava include ʻawa (Hawaiʻi), ʻava (Samoa), yaqona or yagona (Fiji), sakau (Pohnpei), seka (Kosrae), and malok or malogu. Kava is consumed for its sedating effects throughout the Pacific Ocean cultures of Polynesia, including Hawaii, Vanuatu, Melanesia, and some parts of Micronesia, such as Pohnpei and Kosrae.

Kavalactone

Kavalactones are a class of lactone compounds found in the kava shrub. Kavalactones are under research for potential to have various psychotropic effects, including anxiolytic and sedative/hypnotic activities.

Gamma-glutamyltransferase is a transferase that catalyzes the transfer of gamma-glutamyl functional groups from molecules such as glutathione to an acceptor that may be an amino acid, a peptide or water. GGT plays a key role in the gamma-glutamyl cycle, a pathway for the synthesis and degradation of glutathione as well as drug and xenobiotic detoxification. Other lines of evidence indicate that GGT can also exert a pro-oxidant role, with regulatory effects at various levels in cellular signal transduction and cellular pathophysiology. This transferase is found in many tissues, the most notable one being the liver, and has significance in medicine as a diagnostic marker.

Hepatotoxicity Liver damage caused by a drug or chemical

Hepatotoxicity implies chemical-driven liver damage. Drug-induced liver injury is a cause of acute and chronic liver disease caused specifically by medications.

GABA receptor agonist

A GABA receptor agonist is a drug that is an agonist for one or more of the GABA receptors, producing typically sedative effects, and may also cause other effects such as anxiolytic, anticonvulsant, and muscle relaxant effects. There are three receptors of the gamma-aminobutyric acid. The two receptors GABA-α and GABA-ρ are ion channels that are permeable to chloride ions which reduces neuronal excitability. The GABA-β receptor belongs to the class of G-Protein coupled receptors that inhibit adenylyl cyclase, therefore leading to decreased cyclic adenosine monophosphate (cAMP). GABA-α and GABA-ρ receptors produce sedative and hypnotic effects and have anti-convulsion properties. GABA-β receptors also produce sedative effects. Furthermore, they lead to changes in gene transcription.

Monoamine oxidase B

Monoamine oxidase B, also known as MAOB, is an enzyme that in humans is encoded by the MAOB gene.

Desmethoxyyangonin Chemical compound

Desmethoxyyangonin or 5,6-dehydrokavain is one of the six main kavalactones found in the Piper methysticum (kava) plant.

Kavain Chemical compound

Kavain is the main kavalactone found mostly in the roots of the kava plant.

Kava may refer to:

Pipermethystine Chemical compound

Pipermethystine is a toxic alkaloid present in the aerial (aboveground) portions of the kava plant. It is not a kavalactone, containing no lactone structure. Correctly prepared kava root products will contain almost no pipermethystine.

Flavokavain

Flavokavains are a class of chalconoids found in the kava plant. Currently identified types include flavokavain A, flavokavain B, and flavokavain C.

Dihydrokavain Chemical compound

Dihydrokavain is one of the six major kavalactones found in the kava plant. It appears to contribute significantly to the anxiolytic effects of kava, based on a study in chicks.

Yangonin Chemical compound

Yangonin is one of the six major kavalactones found in the kava plant. It has been shown to possess binding affinity for the cannabinoid receptor CB1 (Ki = 0.72 μM), and selectivity vs. the CB₂ receptor (K(i)>10 μM) where it behaves as an agonist. The CB₁ receptor affinity of yangonin suggests that the endocannabinoid system might contribute to the complex human psychopharmacology of the traditional kava drink and the anxiolytic preparations obtained from the kava plant.

Dihydromethysticin Chemical compound

Dihydromethysticin is one of the six major kavalactones found in the kava plant.

Methysticin Chemical compound

Methysticin is one of the six major kavalactones found in the kava plant. Research suggests that methysticin and the related compound dihydromethysticin have CYP1A1 inducing effects which may be responsible for their toxicity.

Flavokavain A Chemical compound

Flavokavain A is a flavokavain found in the kava plant. It induces apoptosis in bladder cancer cells via a Bax protein-dependent and mitochondria-dependent apoptotic pathway.

Flavokavain C Chemical compound

Flavokavain C is a flavokavain found in the kava plant.

The molecular formula C18H18O5 (molar mass: 314.33 g/mol, exact mass: 314.115424 u) may refer to:

Lava Cola is a cola drink produced in Vanuatu by Vanuatu Beverage Ltd. It contains a kavalactone additive, kava consumption being traditionally important in western Pacific nations. Lava Cola has been described as an "anti-energy drink". Australian media have noted that it "produces the calming effect of kava without the muddy taste," adding that, while kava itself is an acquired taste, Lava Cola may well be suitable for export.

References

  1. Dharmaratne, H. Ranjith W.; N. P. Dhammika Nanayakkara; Ikhlas A. Khan (February 2002). "Kavalactones from Piper methysticum, and their 13C NMR spectroscopic analyses". Phytochemistry. 59 (4): 429–33. doi:10.1016/S0031-9422(01)00443-5. PMID   11830162.
  2. Zhou P., Gross S., Liu J.-H., Yu B.-Y., Feng L.-L., Nolta J., Sharma V., Piwnica-Worms D., Qiu S.X 'Flavokawain B, the hepatotoxic constituent from kava root, induces GSH-sensitive oxidative stress through modulation of IKK/NF-κB and MAPK signaling pathways . FASEB Journal 2010 24:12 (4722-4732)