Posted inUncategorized

Marindinin

July 21, 2017
Common Name

Marindinin Description

Marindinin is found in beverages. Marindinin is found in the roots of kava (Piper methysticum). FDA advises against use of kava in food due to potential risk of severe liver damage (2002) Marindinin belongs to the family of Pyrans. These are compounds containing a pyran ring, which is a six-member heterocyclic, non-aromatic ring with five carbon atoms, one oxygen atom and two ring double bonds. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Structure for HMDB29504 (Marindinin)

Synonyms

Value Source 4-Methoxy-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-oneHMDB 5,6-dihydro-4-Methoxy-6-phenethyl-2H-pyran-2-oneHMDB 7,8-dihydro-KawainHMDB 7,8-DihydrokavainHMDB 7,8-DihydrokawainHMDB dihydro-KavainHMDB dihydro-KawainHMDB DihydrokavainHMDB DihydrokawainHMDB

Chemical Formlia

C14H16O3 Average Molecliar Weight

232.275 Monoisotopic Molecliar Weight

232.109944378 IUPAC Name

4-methoxy-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-one Traditional Name

dihydrokavain CAS Registry Number

587-63-3 SMILES

COC1=CC(=O)OC(CCC2=CC=CC=C2)C1

InChI Identifier

InChI=1S/C14H16O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-6,10,12H,7-9H2,1H3

InChI Key

VOOYTQRREPYRIW-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as kavalactones. These are lactones, which is structurally characterized by a benzene ring and a pyranone moiety, linked to each other to form a 4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one skeleton. Kingdom

Chemical entities Super Class

Organic compounds Class

Phenylpropanoids and polyketides Sub Class

Kavalactones Direct Parent

Kavalactones Alternative Parents

  • Dihydropyranones
  • Benzene and substituted derivatives
  • Vinylogous esters
  • Enoate esters
  • Lactones
  • Oxacyclic compounds
  • Monocarboxylic acids and derivatives
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • Kavalactone
  • Dihydropyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Vinylogous ester
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Lactone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Endogenous

  • Food

    • Biofunction

    Not Available Application

  • Nutrient

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Not Available Experimental Properties

    Property Value Reference Melting Point56 – 60 °CNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.041 mg/mLALOGPS logP2.91ALOGPS logP2.56ChemAxon logS-3.8ALOGPS pKa (Strongest Acidic)16.43ChemAxon pKa (Strongest Basic)-4.8ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count2ChemAxon Hydrogen Donor Count0ChemAxon Polar Surface Area35.53 Å2ChemAxon Rotatable Bond Count4ChemAxon Refractivity66.4 m3·mol-1ChemAxon Polarizability25.35 Å3ChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-001i-0590000000-cdb149e3549ebc48df46View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-0159-1900000000-5f9a595ba9bd7424a337View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-0kvo-9800000000-26a9688f8a322373262eView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-001i-0690000000-1a1d0e9cea6a50a7b0d4View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-000x-9440000000-113393a90e3c0732dd4dView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-0536-9600000000-9fba2cac2d065519983cView in MoNA

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

    Not Available Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations Not Available Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    FDB000639 KNApSAcK ID

    C00029583 Chemspider ID

    88817 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB29504 Metagene Link

    HMDB29504 METLIN ID

    Not Available PubChem Compound

    98356 PDB ID

    Not Available ChEBI ID

    862793

    Product: Ezutromid

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Backhauss C, Krieglstein J: Extract of kava (Piper methysticum) and its methysticin constituents protect brain tissue against ischemic damage in rodents. Eur J Pharmacol. 1992 May 14;215(2-3):265-9. [PubMed:1396990 ]
    2. Boonen G, Haberlein H: Influence of genuine kavapyrone enantiomers on the GABA-A binding site. Planta Med. 1998 Aug;64(6):504-6. [PubMed:9776662 ]
    3. Hu L, Jhoo JW, Ang CY, Dinovi M, Mattia A: Determination of six kavalactones in dietary supplements and selected functional foods containing Piper methysticum by isocratic liquid chromatography with internal standard. J AOAC Int. 2005 Jan-Feb;88(1):16-25. [PubMed:15759721 ]
    4. de Jager LS, Perfetti GA, Diachenko GW: LC-UV and LC-MS analysis of food and drink products containing kava. Food Addit Contam. 2004 Oct;21(10):921-34. [PubMed:15712517 ]
    5. Weiss J, Sauer A, Frank A, Unger M: Extracts and kavalactones of Piper methysticum G. Forst (kava-kava) inhibit P-glycoprotein in vitro. Drug Metab Dispos. 2005 Nov;33(11):1580-3. Epub 2005 Jul 28. [PubMed:16051732 ]
    6. Kato K, Motodate S, Mochida T, Kobayashi T, Akita H: Intermolecular methoxycarbonylation of terminal alkynes catalyzed by palladium(II) bis(oxazoline) complexes. Angew Chem Int Ed Engl. 2009;48(18):3326-8. doi: 10.1002/anie.200806080. [PubMed:19191366 ]
    7. Lin L, Chen Z, Yang X, Liu X, Feng X: Efficient enantioselective hetero-Diels-Alder reaction of Brassards diene with aliphatic aldehydes: a one-step synthesis of (R)-(+)-kavain and (S)-(+)-dihydrokavain. Org Lett. 2008 Mar 20;10(6):1311-4. doi: 10.1021/ol8002282. Epub 2008 Feb 28. [PubMed:18303910 ]
    8. Du H, Zhao D, Ding K: Enantioselective catalysis of the hetero-Diels-Alder reaction between Brassards diene and aldehydes by hydrogen-bonding activation: a one-step synthesis of (S)-(+)-dihydrokawain. Chemistry. 2004 Nov 19;10(23):5964-70. [PubMed:15487027 ]
    9. Herath W, Ferreira D, Mikell JR, Khan IA: Microbial metabolism. Part 5. Dihydrokawain. Chem Pharm Bull (Tokyo). 2004 Nov;52(11):1372-4. [PubMed:15516767 ]
    10. Uebelhack R, Franke L, Schewe HJ: Inhibition of platelet MAO-B by kava pyrone-enriched extract from Piper methysticum Forster (kava-kava). Pharmacopsychiatry. 1998 Sep;31(5):187-92. [PubMed:9832350 ]
    11. Jamieson DD, Duffield PH: The antinociceptive actions of kava components in mice. Clin Exp Pharmacol Physiol. 1990 Jul;17(7):495-507. [PubMed:2401103 ]
    12. Bobeldijk I, Boonzaaijer G, Spies-Faber EJ, Vaes WH: Determination of kava lactones in food supplements by liquid chromatography-atmospheric pressure chemical ionisation tandem mass spectrometry. J Chromatogr A. 2005 Mar 4;1067(1-2):107-14. [PubMed:15844515 ]
    13. Li Y, Mei H, Wu Q, Zhang S, Fang JL, Shi L, Guo L: Methysticin and 7,8-dihydromethysticin are two major kavalactones in kava extract to induce CYP1A1. Toxicol Sci. 2011 Dec;124(2):388-99. doi: 10.1093/toxsci/kfr235. Epub 2011 Sep 9. [PubMed:21908763 ]
    14. Wu D, Yu L, Nair MG, DeWitt DL, Ramsewak RS: Cyclooxygenase enzyme inhibitory compounds with antioxidant activities from Piper methysticum (kava kava) roots. Phytomedicine. 2002 Jan;9(1):41-7. [PubMed:11924763 ]
    15. Folmer F, Blasius R, Morceau F, Tabudravu J, Dicato M, Jaspars M, Diederich M: Inhibition of TNFalpha-induced activation of nuclear factor kappaB by kava (Piper methysticum) derivatives. Biochem Pharmacol. 2006 Apr 14;71(8):1206-18. Epub 2006 Feb 7. [PubMed:16464438 ]
    16. Baum SS, Hill R, Rommelspacher H: Effect of kava extract and individual kavapyrones on neurotransmitter levels in the nucleus accumbens of rats. Prog Neuropsychopharmacol Biol Psychiatry. 1998 Oct;22(7):1105-20. [PubMed:9829291 ]
    17. Otoguro K, Iwatsuki M, Ishiyama A, Namatame M, Nishihara-Tsukashima A, Kiyohara H, Hashimoto T, Asakawa Y, Omura S, Yamada H: In vitro antitrypanosomal activity of some phenolic compounds from propolis and lactones from Fijian Kawa (Piper methysticum). J Nat Med. 2012 Jul;66(3):558-61. doi: 10.1007/s11418-011-0613-z. Epub 2011 Nov 25. [PubMed:22116743 ]
    18. Ma Y, Sachdeva K, Liu J, Ford M, Yang D, Khan IA, Chichester CO, Yan B: Desmethoxyyangonin and dihydromethysticin are two major pharmacological kavalactones with marked activity on the induction of CYP3A23. Drug Metab Dispos. 2004 Nov;32(11):1317-24. Epub 2004 Jul 28. [PubMed:15282211 ]
    19. Hashimoto T, Suganuma M, Fujiki H, Yamada M, Kohno T, Asakawa Y: Isolation and synthesis of TNF-alpha release inhibitors from Fijian kawa (Piper methysticum). Phytomedicine. 2003 May;10(4):309-17. [PubMed:12809361 ]
    20. Feltenstein MW, Lambdin LC, Ganzera M, Ranjith H, Dharmaratne W, Nanayakkara NP, Khan IA, Sufka KJ: Anxiolytic properties of Piper methysticum extract samples and fractions in the chick social-separation-stress procedure. Phytother Res. 2003 Mar;17(3):210-6. [PubMed:12672148 ]
    21. Xuan TD, Elzaawely AA, Fukuta M, Tawata S: Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum). J Agric Food Chem. 2006 Feb 8;54(3):720-5. [PubMed:16448174 ]
    22. Arai Y, Masuda T, Yoneda S, Masaki Y, Shiro M: Asymmetric synthesis of (+)-dihydrokawain-5-ol. J Org Chem. 2000 Jan 14;65(1):258-62. [PubMed:10813926 ]
    23. Yuan CS, Dey L, Wang A, Mehendale S, Xie JT, Aung HH, Ang-Lee MK: Kavalactones and dihydrokavain modulate GABAergic activity in a rat gastric-brainstem preparation. Planta Med. 2002 Dec;68(12):1092-6. [PubMed:12494336 ]
    24. Teschke R, Lebot V: Proposal for a kava quality standardization code. Food Chem Toxicol. 2011 Oct;49(10):2503-16. doi: 10.1016/j.fct.2011.06.075. Epub 2011 Jul 3. [PubMed:21756963 ]
    25. Xuan TD, Chung IM, Khanh TD, Tawata S: Identification of phytotoxic substances from early growth of barnyard grass (Echinochloa crusgalli) root exudates. J Chem Ecol. 2006 Apr;32(4):895-906. Epub 2006 May 5. [PubMed:16718576 ]
    26. Whittaker P, Clarke JJ, San RH, Betz JM, Seifried HE, de Jager LS, Dunkel VC: Evaluation of commercial kava extracts and kavalactone standards for mutagenicity and toxicity using the mammalian cell gene mutation assay in L5178Y mouse lymphoma cells. Food Chem Toxicol. 2008 Jan;46(1):168-74. Epub 2007 Jul 31. [PubMed:17822821 ]
    27. Keledjian J, Duffield PH, Jamieson DD, Lidgard RO, Duffield AM: Uptake into mouse brain of four compounds present in the psychoactive beverage kava. J Pharm Sci. 1988 Dec;77(12):1003-6. [PubMed:3244102 ]
    28. Pescitelli G, Bilia AR, Bergonzi MC, Vincieri FF, Di Bari L: Cyclodextrins as carriers for kavalactones in aqueous media: spectroscopic characterization of (S)-7,8-dihydrokavain and beta-cyclodextrin inclusion complex. J Pharm Biomed Anal. 2010 Aug 1;52(4):479-83. doi: 10.1016/j.jpba.2010.01.037. Epub 2010 Feb 1. [PubMed:20185265 ]
    29. Rasmussen AK, Scheline RR, Solheim E, Hansel R: Metabolism of some kava pyrones in the rat. Xenobiotica. 1979 Jan;9(1):1-16. [PubMed:760318 ]
    30. Warburton E, Bristow T: Fourier transform ion cyclotron resonance mass spectrometry for the characterisation of kavalactones in the kava plant: elemental formulae confirmation by dual spray accurate mass measurement and structural confirmation by infrared multiphoton dissociation and sustained off-resonance irradiation collision induced dissociation. Eur J Mass Spectrom (Chichester). 2006;12(4):223-33. [PubMed:17057279 ]
    31. Tarbah F, Mahler H, Kardel B, Weinmann W, Hafner D, Daldrup T: Kinetics of kavain and its metabolites after oral application. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jun 5;789(1):115-30. [PubMed:12726850 ]
    32. Haberlein H, Boonen G, Beck MA: Piper methysticum: enantiomeric separation of kavapyrones by high performance liquid chromatography. Planta Med. 1997 Feb;63(1):63-5. [PubMed:17252330 ]
    33. Johnson BM, Qiu SX, Zhang S, Zhang F, Burdette JE, Yu L, Bolton JL, van Breemen RB: Identification of novel electrophilic metabolites of piper methysticum Forst (Kava). Chem Res Toxicol. 2003 Jun;16(6):733-40. [PubMed:12807356 ]
    34. Singh RP, Singh VK: Facile one-step synthesis of beta-alkoxy lactone via sequential lactonization and 1,4-addition of alkoxide group: total synthesis of all stereoisomers of dihydrokawain-5-ol. J Org Chem. 2004 May 14;69(10):3425-30. [PubMed:15132552 ]
    35. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

    PMID: 17645497

    Last updated on
    Posted inUncategorized

    Marindinin

    July 21, 2017
    Common Name

    Marindinin Description

    Marindinin is found in beverages. Marindinin is found in the roots of kava (Piper methysticum). FDA advises against use of kava in food due to potential risk of severe liver damage (2002) Marindinin belongs to the family of Pyrans. These are compounds containing a pyran ring, which is a six-member heterocyclic, non-aromatic ring with five carbon atoms, one oxygen atom and two ring double bonds. Structure

    MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

    Structure for HMDB29504 (Marindinin)

    Synonyms

    Value Source 4-Methoxy-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-oneHMDB 5,6-dihydro-4-Methoxy-6-phenethyl-2H-pyran-2-oneHMDB 7,8-dihydro-KawainHMDB 7,8-DihydrokavainHMDB 7,8-DihydrokawainHMDB dihydro-KavainHMDB dihydro-KawainHMDB DihydrokavainHMDB DihydrokawainHMDB

    Chemical Formlia

    C14H16O3 Average Molecliar Weight

    232.275 Monoisotopic Molecliar Weight

    232.109944378 IUPAC Name

    4-methoxy-6-(2-phenylethyl)-5,6-dihydro-2H-pyran-2-one Traditional Name

    dihydrokavain CAS Registry Number

    587-63-3 SMILES

    COC1=CC(=O)OC(CCC2=CC=CC=C2)C1

    InChI Identifier

    InChI=1S/C14H16O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-6,10,12H,7-9H2,1H3

    InChI Key

    VOOYTQRREPYRIW-UHFFFAOYSA-N Chemical Taxonomy Description

    This compound belongs to the class of chemical entities known as kavalactones. These are lactones, which is structurally characterized by a benzene ring and a pyranone moiety, linked to each other to form a 4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one skeleton. Kingdom

    Chemical entities Super Class

    Organic compounds Class

    Phenylpropanoids and polyketides Sub Class

    Kavalactones Direct Parent

    Kavalactones Alternative Parents

  • Dihydropyranones
  • Benzene and substituted derivatives
  • Vinylogous esters
  • Enoate esters
  • Lactones
  • Oxacyclic compounds
  • Monocarboxylic acids and derivatives
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • Kavalactone
  • Dihydropyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Vinylogous ester
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Lactone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Endogenous

  • Food

    • Biofunction

    Not Available Application

  • Nutrient

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Not Available Experimental Properties

    Property Value Reference Melting Point56 – 60 °CNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.041 mg/mLALOGPS logP2.91ALOGPS logP2.56ChemAxon logS-3.8ALOGPS pKa (Strongest Acidic)16.43ChemAxon pKa (Strongest Basic)-4.8ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count2ChemAxon Hydrogen Donor Count0ChemAxon Polar Surface Area35.53 Å2ChemAxon Rotatable Bond Count4ChemAxon Refractivity66.4 m3·mol-1ChemAxon Polarizability25.35 Å3ChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-001i-0590000000-cdb149e3549ebc48df46View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-0159-1900000000-5f9a595ba9bd7424a337View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-0kvo-9800000000-26a9688f8a322373262eView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-001i-0690000000-1a1d0e9cea6a50a7b0d4View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-000x-9440000000-113393a90e3c0732dd4dView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-0536-9600000000-9fba2cac2d065519983cView in MoNA

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

    Not Available Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations Not Available Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    FDB000639 KNApSAcK ID

    C00029583 Chemspider ID

    88817 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB29504 Metagene Link

    HMDB29504 METLIN ID

    Not Available PubChem Compound

    98356 PDB ID

    Not Available ChEBI ID

    862793

    Product: Ezutromid

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Backhauss C, Krieglstein J: Extract of kava (Piper methysticum) and its methysticin constituents protect brain tissue against ischemic damage in rodents. Eur J Pharmacol. 1992 May 14;215(2-3):265-9. [PubMed:1396990 ]
    2. Boonen G, Haberlein H: Influence of genuine kavapyrone enantiomers on the GABA-A binding site. Planta Med. 1998 Aug;64(6):504-6. [PubMed:9776662 ]
    3. Hu L, Jhoo JW, Ang CY, Dinovi M, Mattia A: Determination of six kavalactones in dietary supplements and selected functional foods containing Piper methysticum by isocratic liquid chromatography with internal standard. J AOAC Int. 2005 Jan-Feb;88(1):16-25. [PubMed:15759721 ]
    4. de Jager LS, Perfetti GA, Diachenko GW: LC-UV and LC-MS analysis of food and drink products containing kava. Food Addit Contam. 2004 Oct;21(10):921-34. [PubMed:15712517 ]
    5. Weiss J, Sauer A, Frank A, Unger M: Extracts and kavalactones of Piper methysticum G. Forst (kava-kava) inhibit P-glycoprotein in vitro. Drug Metab Dispos. 2005 Nov;33(11):1580-3. Epub 2005 Jul 28. [PubMed:16051732 ]
    6. Kato K, Motodate S, Mochida T, Kobayashi T, Akita H: Intermolecular methoxycarbonylation of terminal alkynes catalyzed by palladium(II) bis(oxazoline) complexes. Angew Chem Int Ed Engl. 2009;48(18):3326-8. doi: 10.1002/anie.200806080. [PubMed:19191366 ]
    7. Lin L, Chen Z, Yang X, Liu X, Feng X: Efficient enantioselective hetero-Diels-Alder reaction of Brassards diene with aliphatic aldehydes: a one-step synthesis of (R)-(+)-kavain and (S)-(+)-dihydrokavain. Org Lett. 2008 Mar 20;10(6):1311-4. doi: 10.1021/ol8002282. Epub 2008 Feb 28. [PubMed:18303910 ]
    8. Du H, Zhao D, Ding K: Enantioselective catalysis of the hetero-Diels-Alder reaction between Brassards diene and aldehydes by hydrogen-bonding activation: a one-step synthesis of (S)-(+)-dihydrokawain. Chemistry. 2004 Nov 19;10(23):5964-70. [PubMed:15487027 ]
    9. Herath W, Ferreira D, Mikell JR, Khan IA: Microbial metabolism. Part 5. Dihydrokawain. Chem Pharm Bull (Tokyo). 2004 Nov;52(11):1372-4. [PubMed:15516767 ]
    10. Uebelhack R, Franke L, Schewe HJ: Inhibition of platelet MAO-B by kava pyrone-enriched extract from Piper methysticum Forster (kava-kava). Pharmacopsychiatry. 1998 Sep;31(5):187-92. [PubMed:9832350 ]
    11. Jamieson DD, Duffield PH: The antinociceptive actions of kava components in mice. Clin Exp Pharmacol Physiol. 1990 Jul;17(7):495-507. [PubMed:2401103 ]
    12. Bobeldijk I, Boonzaaijer G, Spies-Faber EJ, Vaes WH: Determination of kava lactones in food supplements by liquid chromatography-atmospheric pressure chemical ionisation tandem mass spectrometry. J Chromatogr A. 2005 Mar 4;1067(1-2):107-14. [PubMed:15844515 ]
    13. Li Y, Mei H, Wu Q, Zhang S, Fang JL, Shi L, Guo L: Methysticin and 7,8-dihydromethysticin are two major kavalactones in kava extract to induce CYP1A1. Toxicol Sci. 2011 Dec;124(2):388-99. doi: 10.1093/toxsci/kfr235. Epub 2011 Sep 9. [PubMed:21908763 ]
    14. Wu D, Yu L, Nair MG, DeWitt DL, Ramsewak RS: Cyclooxygenase enzyme inhibitory compounds with antioxidant activities from Piper methysticum (kava kava) roots. Phytomedicine. 2002 Jan;9(1):41-7. [PubMed:11924763 ]
    15. Folmer F, Blasius R, Morceau F, Tabudravu J, Dicato M, Jaspars M, Diederich M: Inhibition of TNFalpha-induced activation of nuclear factor kappaB by kava (Piper methysticum) derivatives. Biochem Pharmacol. 2006 Apr 14;71(8):1206-18. Epub 2006 Feb 7. [PubMed:16464438 ]
    16. Baum SS, Hill R, Rommelspacher H: Effect of kava extract and individual kavapyrones on neurotransmitter levels in the nucleus accumbens of rats. Prog Neuropsychopharmacol Biol Psychiatry. 1998 Oct;22(7):1105-20. [PubMed:9829291 ]
    17. Otoguro K, Iwatsuki M, Ishiyama A, Namatame M, Nishihara-Tsukashima A, Kiyohara H, Hashimoto T, Asakawa Y, Omura S, Yamada H: In vitro antitrypanosomal activity of some phenolic compounds from propolis and lactones from Fijian Kawa (Piper methysticum). J Nat Med. 2012 Jul;66(3):558-61. doi: 10.1007/s11418-011-0613-z. Epub 2011 Nov 25. [PubMed:22116743 ]
    18. Ma Y, Sachdeva K, Liu J, Ford M, Yang D, Khan IA, Chichester CO, Yan B: Desmethoxyyangonin and dihydromethysticin are two major pharmacological kavalactones with marked activity on the induction of CYP3A23. Drug Metab Dispos. 2004 Nov;32(11):1317-24. Epub 2004 Jul 28. [PubMed:15282211 ]
    19. Hashimoto T, Suganuma M, Fujiki H, Yamada M, Kohno T, Asakawa Y: Isolation and synthesis of TNF-alpha release inhibitors from Fijian kawa (Piper methysticum). Phytomedicine. 2003 May;10(4):309-17. [PubMed:12809361 ]
    20. Feltenstein MW, Lambdin LC, Ganzera M, Ranjith H, Dharmaratne W, Nanayakkara NP, Khan IA, Sufka KJ: Anxiolytic properties of Piper methysticum extract samples and fractions in the chick social-separation-stress procedure. Phytother Res. 2003 Mar;17(3):210-6. [PubMed:12672148 ]
    21. Xuan TD, Elzaawely AA, Fukuta M, Tawata S: Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum). J Agric Food Chem. 2006 Feb 8;54(3):720-5. [PubMed:16448174 ]
    22. Arai Y, Masuda T, Yoneda S, Masaki Y, Shiro M: Asymmetric synthesis of (+)-dihydrokawain-5-ol. J Org Chem. 2000 Jan 14;65(1):258-62. [PubMed:10813926 ]
    23. Yuan CS, Dey L, Wang A, Mehendale S, Xie JT, Aung HH, Ang-Lee MK: Kavalactones and dihydrokavain modulate GABAergic activity in a rat gastric-brainstem preparation. Planta Med. 2002 Dec;68(12):1092-6. [PubMed:12494336 ]
    24. Teschke R, Lebot V: Proposal for a kava quality standardization code. Food Chem Toxicol. 2011 Oct;49(10):2503-16. doi: 10.1016/j.fct.2011.06.075. Epub 2011 Jul 3. [PubMed:21756963 ]
    25. Xuan TD, Chung IM, Khanh TD, Tawata S: Identification of phytotoxic substances from early growth of barnyard grass (Echinochloa crusgalli) root exudates. J Chem Ecol. 2006 Apr;32(4):895-906. Epub 2006 May 5. [PubMed:16718576 ]
    26. Whittaker P, Clarke JJ, San RH, Betz JM, Seifried HE, de Jager LS, Dunkel VC: Evaluation of commercial kava extracts and kavalactone standards for mutagenicity and toxicity using the mammalian cell gene mutation assay in L5178Y mouse lymphoma cells. Food Chem Toxicol. 2008 Jan;46(1):168-74. Epub 2007 Jul 31. [PubMed:17822821 ]
    27. Keledjian J, Duffield PH, Jamieson DD, Lidgard RO, Duffield AM: Uptake into mouse brain of four compounds present in the psychoactive beverage kava. J Pharm Sci. 1988 Dec;77(12):1003-6. [PubMed:3244102 ]
    28. Pescitelli G, Bilia AR, Bergonzi MC, Vincieri FF, Di Bari L: Cyclodextrins as carriers for kavalactones in aqueous media: spectroscopic characterization of (S)-7,8-dihydrokavain and beta-cyclodextrin inclusion complex. J Pharm Biomed Anal. 2010 Aug 1;52(4):479-83. doi: 10.1016/j.jpba.2010.01.037. Epub 2010 Feb 1. [PubMed:20185265 ]
    29. Rasmussen AK, Scheline RR, Solheim E, Hansel R: Metabolism of some kava pyrones in the rat. Xenobiotica. 1979 Jan;9(1):1-16. [PubMed:760318 ]
    30. Warburton E, Bristow T: Fourier transform ion cyclotron resonance mass spectrometry for the characterisation of kavalactones in the kava plant: elemental formulae confirmation by dual spray accurate mass measurement and structural confirmation by infrared multiphoton dissociation and sustained off-resonance irradiation collision induced dissociation. Eur J Mass Spectrom (Chichester). 2006;12(4):223-33. [PubMed:17057279 ]
    31. Tarbah F, Mahler H, Kardel B, Weinmann W, Hafner D, Daldrup T: Kinetics of kavain and its metabolites after oral application. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jun 5;789(1):115-30. [PubMed:12726850 ]
    32. Haberlein H, Boonen G, Beck MA: Piper methysticum: enantiomeric separation of kavapyrones by high performance liquid chromatography. Planta Med. 1997 Feb;63(1):63-5. [PubMed:17252330 ]
    33. Johnson BM, Qiu SX, Zhang S, Zhang F, Burdette JE, Yu L, Bolton JL, van Breemen RB: Identification of novel electrophilic metabolites of piper methysticum Forst (Kava). Chem Res Toxicol. 2003 Jun;16(6):733-40. [PubMed:12807356 ]
    34. Singh RP, Singh VK: Facile one-step synthesis of beta-alkoxy lactone via sequential lactonization and 1,4-addition of alkoxide group: total synthesis of all stereoisomers of dihydrokawain-5-ol. J Org Chem. 2004 May 14;69(10):3425-30. [PubMed:15132552 ]
    35. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

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