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(+)-Kavain Sale

(Synonyms: 醉椒素) 目录号 : GC30933

A kavalactone with diverse biological activities

(+)-Kavain Chemical Structure

Cas No.:500-64-1

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10mM (in 1mL DMSO)
¥491.00
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5mg
¥446.00
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10mg
¥625.00
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产品描述

Kavain is a kavalactone and the major constituent of the pepper plant kava (P. methysticum) and has diverse biological activities.1,2,3,4 It is a positive allosteric modulator of α4β2δ subunit-containing GABAA receptors with EC50 values of 25 and 59 ?M in the presence and absence of 300 ?M kavain, respectively, in Xenopus oocytes expressing human receptors.1 Kavain reduces growth of WPMY-1 prostate cancer cells (IC50 = 5.2 ?g/ml).2 It reduces LPS-induced TNF-α production in primary murine macrophages in a concentration-dependent manner.3 In vivo, kavain (1 mg/animal) reduces hind paw swelling and TNF-α production in wild-type, but not Erk-/-, mice in a mouse model of collagen-induced arthritis. Kavain also reduces acetic acid-induced abdominal constrictions in mice (ED50= 15.71 mg/kg).4

1.Chua, H.C., Christensen, E.T., Hoestgaard-Jensen, K., et al.Kavain, the major constituent of the anxiolytic kava extract, potentiates GABAA receptors: Functional characteristics and molecular mechanismPLoS One11(6)e0157700(2016) 2.Li, X., Liu, Z., Xu, X., et al.Kava components down-regulate expression of AR and AR splice variants and reduce growth in patient-derived prostate cancer xenografts in micePLoS One7(2)e31213(2012) 3.Tang, X., and Amar, S.Kavain Inhibition of LPS-Induced TNF-α via ERK/LITAFToxicol. Res. (Camb).5(1)188-196(2016) 4.Kormann, E.C., de Aguiar Amaral, P., David, M., et al.Kavain analogues as potential analgesic agentsPharmacol. Rep.64(6)1419-1426(2012)

Chemical Properties

Cas No. 500-64-1 SDF
别名 醉椒素
Canonical SMILES O=C1C=C(OC)C[C@H](/C=C/C2=CC=CC=C2)O1
分子式 C14H14O3 分子量 230.26
溶解度 DMSO : ≥ 125 mg/mL (542.86 mM) 储存条件 Store at -20°C
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1 mM 4.3429 mL 21.7146 mL 43.4292 mL
5 mM 0.8686 mL 4.3429 mL 8.6858 mL
10 mM 0.4343 mL 2.1715 mL 4.3429 mL
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Research Update

Kavain Interference with Amphetamine Immunoassay

Introduction: We encountered unexpected false positive urine results in three patients for amphetamine-type substances by immunoassay, measured as part of community drug prevention programmes. Kavain was identified in all three urine samples by gas chromatography mass spectrometry (GC-MS). No other potential cross-reactants were found.Kavain is a kava-lactone present in kava, a ceremonial and recreational drink derived from roots and stem of the plant Piper Methysticum. It is consumed regularly by many indigenous Pacific and Australian Aboriginal communities. Methods: Urine immunoassay was performed on a Beckman Coulter AU480 Analyser using CEDIA amphetamine-type substances reagent and DRI ethanol reagent. Three different kava powders were purchased from local kava clubs and dissolved in ethanol, then evaporated and reconstituted in blank urine and analysed by immunoassay, GC-MS for amphetamine-type substances. Additionally authentic kavain standard was also tested for cross reactivity by immunoassay and analysed by GC-MS to compare the mass fragmentation pattern and retention time with the kava powder and patient specimens. Results and discussion: The patient urine samples tested positive by CEDIA immunoassay for amphetamines. However, when analysed by GCMS they were negative for amphetamine-type but contained kavain.The kava powders and kavain standard all cross reacted with the amphetamine immunoassay to give falsely detected results. GCMS did not identify any amphetamine-type compounds in any of the Kava powders nor in the kavain standard. Conclusion: To our knowledge, this is the first report of false positive amphetamine measurements due to kavain, a component of the kava drink, widely consumed in Oceania and Australasia.

Protective effect of kavain in meristematic cells of Allium cepa L

Kavain is one of the main kavalactones of Piper methysticum (Piperaceae) with anxiolytic, analgesic, and antioxidant activities. Therefore, the aim of the study was to evaluate the cytotoxic, mutagenic, and antimutagenic potential of kavain in Allium cepa cells. Roots of A. cepa were transferred to the negative (2% acetone) and positive (10 ?g/mL of Methylmethanesulfonate, MMS) controls and to the concentrations of kavain (32, 64 and 128 ?g/mL) for 48 h. A total of 5,000 meristematic cells were analyzed under an optical microscope to determine the mitotic index, mean number of chromosomal alterations and percentage of damage reduction. Data were analyzed by Kruskal-Wallis test (p <0.05). All concentrations of kavain were not cytotoxic and did not show significant chromosomal changes when compared to 2% acetone. Kavain showed a cytoprotective effect in the pre (128 μg/mL) and in the post-treatment (32 and 64 μg/mL) and reduced damage against the mutagenic action of MMS in all concentrations of the pre and simultaneous and at the highest of post (128 μg/mL). Kavain promoted a significant reduction in micronuclei, nuclear buds and chromosomal losses in relation to MMS. The observed data indicate the importance of kavain for the inhibition of damage and chemoprevention.

Modulating effect of DL-kavain on the mutagenicity and carcinogenicity induced by doxorubicin in Drosophila melanogaster

Kavain, kavalactone, present in Piper methysticum exhibits anticonvulsive, analgesic, anxiolytic, antiepileptic, antithrombotic, anti-inflammatory and antioxidant properties. Given its importance, the aim of the present study was to assess (1) the mutagenic and carcinogenicity of kavain administered alone and (2) the antimutagenic and anticarcinogenic potential when administered simultaneously with the chemotherapeutic drug doxorubicin (DXR) using the Somatic Mutation and Recombination Test (SMART) and Epithelial Tumor Test (ETT) using Drosophila melanogaster as a model system. Third-stage larvae from a standard (ST) and high metabolic bioactivation (HB) crosses were treated with different kavain concentrations (32, 64 or 128 μg/ml), alone or in conjunction with DXR (0.125 mg/ml). In ST descendants, kavain produced no significant mutagenic or recombinogenic effects. In the HB cross, mutagenic activity was observed at kavain concentrations of 64 and 128 μg/ml. In the DXR and kavain co-treatment, a modulating effect of the DXR-mediated mutagenic response dependent upon the concentration was detected in both crosses. In ETT, no marked carcinogenic or anticarcinogenic activity was noted for kavain. However, when kavain was combined with DXR synergistic induction of tumors by the chemotherapeutic drug occurred indicating that kavain enhanced the carcinogenic action of DXR.

Kavain Reduces Porphyromonas gingivalis- Induced Adipocyte Inflammation: Role of PGC-1α Signaling

A link between obesity and periodontitis has been suggested because of compromised immune response and chronic inflammation in obese patients. In this study, we evaluated the anti-inflammatory properties of Kavain, an extract from Piper methysticum, on Porphyromonas gingivalis-induced inflammation in adipocytes with special focus on peroxisome proliferation-activated receptor γ coactivator α (PGC-1α) and related pathways. The 3T3-L1 mouse preadipocytes and primary adipocytes harvested from mouse adipose tissue were infected with P. gingivalis, and inflammation (TNF-α; adiponectin/adipokines), oxidative stress, and adipogenic marker (FAS, CEBPα, and PPAR-γ) expression were measured. Furthermore, effect of PGC-1α knockdown on Kavain action was evaluated. Results showed that P. gingivalis worsens adipocyte dysfunction through increase of TNF-α, IL-6, and iNOS and decrease of PGC-1α and adiponectin. Interestingly, although Kavain obliterated P. gingivalis-induced proinflammatory effects in wild-type cells, Kavain did not affect PGC-1α-deficient cells, strongly advocating for Kavain effects being mediated by PGC-1α. In vivo adipocytes challenged with i.p. injection of P. gingivalis alone or P. gingivalis and Kavain displayed the same phenotype as in vitro adipocytes. Altogether, our findings established anti-inflammatory and antioxidant effects of Kavain on adipocytes and emphasized protective action against P. gingivalis-induced adipogenesis. The use of compounds such as Kavain offer a portal to potential therapeutic approaches to counter chronic inflammation in obesity-related diseases.

Biopharmaceutical evaluation of kavain in Piper methysticum G. Forst dried extract: Equilibrium solubility and intestinal permeability in Caco-2 cell model

Ethnopharmacological relevance: Piper methysticum G. Forst, popularly known as kava, is a traditional medicinal plant native from South Pacific islands and widely used to treat anxiety, depression and stress. The psychoactive properties are related to the kavalactones, mainly kavain.
Aim of the study: To evaluate the biopharmaceutical properties of synthetic kavain and when present in kava dried extracts by means of equilibrium solubility and intestinal permeability studies in the Caco-2 cell model.
Materials and methods: The equilibrium solubility of kavain was performed using a shake flask incubator at 37 °C in different media at physiological pH range (1.2-6.8). The intestinal permeability of kavain evaluated in Caco-2 cells in the presence and absence of the P-glycoprotein inhibitor verapamil. Kavain concentrations were determined by reversed phase high performance liquid chromatography (HPLC).
Results: HPLC methods were developed and fully validated for kavain quantitation. Kavain demonstrated low solubility and the pH of the aqueous media did not affect its solubility. Kavain was found to be highly permeable and efflux of kavain mediated by P-glycoprotein was not significant during intestinal permeation.
Conclusion: The results of biopharmaceutical studies provided useful information for predicting availability of kavain from the gastrointestinal tract and this compound was ranked as BCS Class II, exhibiting dissolution rate-limited absorption.