Analysis of kavalactones from Piper methysticum (kava-kava)

Bilia, Anna Rita; Scalise, Luca; Bergonzi, Maria Camilla; Vincieri, Franco Francesco

doi:10.1016/j.jchromb.2004.07.038

Cited by 27 publications

(23 citation statements)

References 36 publications

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“…Its biological activities include binding to the gamma-aminobutyric acid receptor (55) and inhibition of noradrenaline uptake (56). The chemical constituents in kava extract are arylethylene-α-pyrones, chalcones and other flavanones, and conjugated diene ketones (57). The kavalactones, which are the substituted 4-methoxy-5,6-dihydro-α-pyrones, are associated with pharmacological activity.…”

Section: Piper Methysticum (Kava Kava)mentioning

confidence: 99%

Activation of Pregnane X Receptor (PXR) and Constitutive Androstane Receptor (CAR) by Herbal Medicines

Chang

2009

AAPS J

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Abstract. Pregnane X receptor (PXR) and constitutive androstane receptor (CAR) are transcription factors that control the expression of a broad array of genes involved not only in transcellular transport and biotransformation of many drugs, other xenochemicals, and endogenous substances, such as bile acid, bilirubin, and certain vitamins, but also in various physiological/pathophysiological processes such as lipid metabolism, glucose homeostasis, and inflammation. Ligands of PXR and CAR are chemicals of diverse structures, including naturally occurring compounds present in herbal medicines. The overall aim of this article is to provide an overview of our current understanding of the role of herbal medicines as modulators of PXR and CAR.

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Section: Piper Methysticum (Kava Kava)mentioning

confidence: 99%

Activation of Pregnane X Receptor (PXR) and Constitutive Androstane Receptor (CAR) by Herbal Medicines

Chang

2009

AAPS J

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“…These kavalactones are the main components of the rhizome and roots of kava (Piper methysticum G. Forst), a Piperaceae common on some Pacific Ocean islands (Bilia et al, 2004). Anthropological evidence suggests that kava has been cultivated and consumed for more than 3000 years.…”

mentioning

confidence: 99%

Kavalactones Protect Neural Cells against Amyloid β Peptide-Induced Neurotoxicity via Extracellular Signal-Regulated Kinase 1/2-Dependent Nuclear Factor Erythroid 2-Related Factor 2 Activation

Wruck¹,

Götz²,

Herdegen³

et al. 2008

Mol Pharmacol

108

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One hallmark of Alzheimer's disease is the accumulation of amyloid ␤-peptide (AP), which can initiate a cascade of oxidative events that may result in neuronal death. Because nuclear factor erythroid 2-related factor 2 (Nrf2) is the major regulator for a battery of genes encoding detoxifying and antioxidative enzymes via binding to the antioxidant response element (ARE), it is of great interest to find nontoxic activators of Nrf2 rendering neuronal cells more resistant to AP toxicity. Using ARE-luciferase assay and Western blot, we provide evidence that the kavalactones methysticin, kavain, and yangonin activate Nrf2 time-and dose-dependently in neural PC-12 and astroglial C6 cells and thereby upregulate cytoprotective genes. Viability and cytotoxicity assays demonstrate that Nrf2 activation is able to protect neural cells from amyloid ␤-(1-42) induced neurotoxicity. Down-regulation of Nrf2 by small hairpin RNA as well as extracellular signal-regulated kinase 1/2 inhibition abolishes cytoprotection. We further give evidence that kavalactone-mediated Nrf2 activation is not dependent on oxidative stress production. Our results demonstrate that kavalactones attenuate amyloid ␤-peptide toxicity by inducing protective gene expression mediated by Nrf2 activation in vitro. These findings indicate that the use of purified kavalactones might be considered as an adjunct therapeutic strategy to combat neural demise in Alzheimer disease and other oxidative stress-related diseases.

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“…20) Melanogenesis stimulation activity of acetone extract was similar to that of 50% ethanolic extract, whereas 70% methanolic extract was inactive indicating that the active ingredients are not hydrophilic substances. The activityguided fractionation of Kava acetone extract led to the isolation of five kavalactones, 5,6-dehydrokawain (1), yangonin (2), (ϩ)-kawain (3), (ϩ)-methysticin (4) and 7,8-epoxyyangonin (5) along with a glucosylsterol, daucosterin (6). Although two groups 7,8) recently reported the isolation of these kavalactones, 1-5, from Kava, the isolation of 6 has not been reported hitherto.…”

Section: Resultsmentioning

confidence: 99%

“…The rhizomes of P. methysticum have been called Kava (Kava-kava or Kawa) in Oceania, and the South Pacific islanders have been traditionally used the rhizome for the preparation of psychoactive beverage in social and ceremonial events. 5) Phytochemicals in P. methysticum have been extensively studied, and a number of kavalactones such as 5,6-dehydrokawain (1), yangonin (2), (ϩ)-kawain (3), (ϩ)-methysticin (4) and 7,8-epoxyyangonin (5) [5][6][7][8] have been isolated. This paper deals with the screening results of melanogenesis activity of Piper species, and the activity-guided fractionation of P. methysticum rhizome extract led to the isolation of active kavalactones, 2 and 5 ( Fig.…”

mentioning

confidence: 99%

Melanogenesis Stimulation in Murine B16 Melanoma Cells by Kava (Piper methysticum) Rhizome Extract and Kavalactones

Matsuda

Hirata

Kawaguchi

et al. 2006

Biological & Pharmaceutical Bulletin

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Melanogenesis stimulation activity of aqueous ethanolic extracts obtained from several different parts of five Piper species, namely Piper longum, P. kadsura, P. methysticum, P. betle, and P. cubeba, were examined by using cultured murine B16 melanoma cells. Among them, the extract of P. methysticum rhizome (Kava) showed potent stimulatory effect on melanogenesis as well as P. nigrum leaf extract. Activity-guided fractionation of Kava extract led to the isolation of two active kavalactones, yangonin (2) and 7,8-epoxyyangonin (5), along with three inactive kavalactones, 5,6-dehydrokawain (1), (؉)-kawain (3) and (؉)-methysticin (4), and a glucosylsterol, daucosterin (6). 7,8-Epoxyyangonin (5) showed a significant stimulatory effect on melanogenesis in B16 melanoma cells. Yangonin (2) exhibited a weak melanogenesis stimulation activity.

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Analysis of kavalactones from Piper methysticum (kava-kava)

Cited by 27 publications

References 36 publications

Activation of Pregnane X Receptor (PXR) and Constitutive Androstane Receptor (CAR) by Herbal Medicines

Activation of Pregnane X Receptor (PXR) and Constitutive Androstane Receptor (CAR) by Herbal Medicines

Kavalactones Protect Neural Cells against Amyloid β Peptide-Induced Neurotoxicity via Extracellular Signal-Regulated Kinase 1/2-Dependent Nuclear Factor Erythroid 2-Related Factor 2 Activation

Melanogenesis Stimulation in Murine B16 Melanoma Cells by Kava (Piper methysticum) Rhizome Extract and Kavalactones

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