Toxicological Actions of Plant-Derived and Anthropogenic Methylenedioxyphenyl-Substituted Chemicals in Mammals and Insects

REFERENCES

• Adams , N. H. , Levi , P. E. and Hodgson , E. 1993 . Differences in induction of three P-450 isozymes by piperonyl butoxide, sesamex. safrole and isosafrole . Pestic. Biochem. Physiol. , 46 : 15 – 26 .
   Web of Science ®Google Scholar
• Andersen , J. F. , Utermohlen , J. G. and Feyereisen , R. 1994 . Expression of house fly CYP6A1 and NADPH-cytochrome P450 reductase in Escherichia coli and reconstitution of an insecticide-metabolizing P450 system . Biochemistry , 33 : 2171 – 77 .
   PubMed Web of Science ®Google Scholar
• Andersen , J. F. , Walding , J. K. , Evans , P. H. , Bowers , W. S. and Feyereisen , R. 1997 . Substrate specificity for the epoxidation of terpenoids and active site topology of house fly cytochrome P450 6A1 . Chem. Res. Toxicol. , 10 : 156 – 64 .
   PubMed Web of Science ®Google Scholar
• Antoniewski , C. , Laval , M. and Lepesant , J.A. 1993 . Structural features critical to the activity of an ecdysone receptor binding site . Insect. Biochem. Mol. Biol. , 23 : 105 – 14 .
   PubMed Web of Science ®Google Scholar
• Atal , C. K. , Dubey , R. K. and Singh , J. 1985 . Biochemical basis of enhanced drug bioavailability by piperine: Evidence that piperine is a potent inhibitor of drug metabolism . J. Pharmacol. Exp. Ther. , 232 : 258 – 62 .
   PubMed Web of Science ®Google Scholar
• Attaluri , S. , Bonala , R. R. , Yang , I. Y. , Lukin , M. A. , Wen , Y. , Grollman , A. P. , Moriya , M. , Iden , C. R. and Johnson , F. 2010 . DNA adducts of aristolochic acid II: Total synthesis and site-specific mutagenesis studies in mammalian cells . Nucleic Acids Res. , 38 : 339 – 52 .
   PubMed Web of Science ®Google Scholar
• Backlund , M. , Johansson , I. , Mkrtchian , S. and Ingelman-Sundberg , M. 1997 . Signal transduction-mediated activation of the aryl hydrocarbon receptor in rat hepatoma H4IIE cells . J. Biol. Chem. , 272 : 31755 – 63 .
   PubMed Web of Science ®Google Scholar
• Baudry , J. , Li , W. , Pan , L. , Berenbaum , M. R. and Schuler , M. A. 2003 . Molecular docking of substrates and inhibitors in the catalytic site of CYP6B1, an insect cytochrome P450 monooxygenase . Protein Eng. , 16 : 577 – 87 .
   PubMedGoogle Scholar
• Benedetti , M. S. , Malnoë , A. and Broillet , A. L. 1977 . Absorption, metabolism and excretion of safrole in the rat and man . Toxicology , 7 : 69 – 83 .
   PubMed Web of Science ®Google Scholar
• Berenbaum , M. R. and Neal , J. J. 1985 . Synergism between myristicin and xanthotoxin, a naturally cooccurring plant toxicant . J. Chem. Ecol. , 11 : 1349 – 58 .
   PubMed Web of Science ®Google Scholar
• Berenbaum , M. R. and Feeny , P. P. 2008 . “ Chemical mediation of host-plant specialization: The Papilionid paradigm in specialization, speciation, and radiation ” . In The evolutionary biology of herbivorous insects , Edited by: Tilmon , K. 3 – 19 . Berkeley : University of California Press .
   Google Scholar
• Bernard , C. B. , Krishanmurty , H. G. , Chauret , D. , Durst , T. , Philogène , B. J. R. , Sánchez-Vindas , P. , Hasbun , C. , Poveda , L. , San Román , L. and Arnason , J. T. 1995 . Insecticidal defenses of Piperaceae from the neotropics . J. Chem. Ecol. , 21 : 801 – 14 .
   PubMed Web of Science ®Google Scholar
• Bernard , C. B. , Arnason , J. T. , Philogène , B. J. R. , Lam , J. and Waddell , T. 1989 . Effect of lignans and other secondary metabolites of the Asteraceae on the mono-oxygenase activity of the european corn borer . Phytochemistry , 28 : 1373 – 77 .
   Web of Science ®Google Scholar
• Bhardwaj , R. K. , Glaeser , H. , Becquemont , L. , Klotz , U. , Gupta , S. K. and Fromm , M. F. 2002 . Piperine, a major constituent of black pepper, inhibits human P-glycoprotein and CYP3A4 . J. Pharmacol. Exp. Ther. , 302 : 645 – 50 .
   PubMed Web of Science ®Google Scholar
• Boberg , E. W. , Miller , E. C. , Miller , J. A. , Poland , A. and Liem , A. 1983 . Strong evidence from studies with brachymorphic mice and pentachlorophenol that 1'-sulfooxysafrole is the major ultimate electrophilic and carcinogenic metabolite of 1'-hydroxysafrole in mouse liver . Cancer Res. , 43 : 5163 – 73 .
   PubMed Web of Science ®Google Scholar
• Borchert , P. , Wislocki , P. G. , Miller , J. A. and Miller , E. C. 1973 . The metabolism of the naturally occurring hepatocarcinogen safrole to 1'-hydroxysafrole and the electrophilic reactivity of 1'-acetoxysafrole . Cancer Res. , 33 : 575 – 89 .
   PubMed Web of Science ®Google Scholar
• Brown , R. P. , McDonnell , C. M. , Berenbaum , M. R. and Schuler , M. A. 2005 . Regulation of an insect cytochrome P450 monooxygenase gene (CYP6B1) by aryl hydrocarbon and xanthotoxin response cascades . Gene , 358 : 39 – 52 .
   PubMed Web of Science ®Google Scholar
• Casida , J. E. , Engel , J. L. , Esaac , E. G. , Kamienski , F. X. and Kuwatsuka , S. 1966 . Methylene-C14-dioxyphenyl compounds: Metabolism in relation to their synergistic action . Science , 153 : 1130 – 33 .
   PubMed Web of Science ®Google Scholar
• Chang , K. M , Wilkinson , C. F. and Hetnarski , K. 1981 . Spectral and inhibitory interactions of methylenedioxyphenyl compounds with southern armyworm (Spodoptera eridania) midgut microsomes . Pestic. Biochem. Physiol. , 15 : 32 – 42 .
   Web of Science ®Google Scholar
• Chatterjee , P. and Franklin , M. R. 2003 . Human cytochrome P450 inhibition and metabolic-intermediate complex formation by goldenseal extract and its methylenedioxyphenyl components . Drug Metab. Dispos. , 31 : 1391 – 97 .
   PubMed Web of Science ®Google Scholar
• Chen , C. L. , Chi , C. W. , Chang , K. W. and Liu , T. Y. 1999 . Safrole-like DNA adducts in oral tissue from oral cancer patients with a betel quid chewing history . Carcinogenesis , 20 : 2331 – 34 .
   PubMed Web of Science ®Google Scholar
• Chen , J.-S. , Berenbaum , M. R. and Schuler , M. A. 2002 . Amino acids in SRS1 and SRS6 are critical for furanocoumarin metabolism by CYP6B1v1, a cytochrome P450 monooxygenase . Insect Mol. Biol. , 11 : 175 – 86 .
   PubMed Web of Science ®Google Scholar
• Chiu , T. L. , Wen , Z. , Rupasinghe , A. G. and Schuler , M. A. 2008 . Comparative molecular modeling of Anopheles gambiae CYP6Z1, a mosquito P450 capable of metabolizing DDT . Proc. Natl Acad. Sci. USA , 105 : 8855 – 60 .
   PubMed Web of Science ®Google Scholar
• Clayton , N. P. , Yoshizawa , K. , Kissling , G. E. , Burka , L. T. , Chan , P. C. and Nyska , A. 2007 . Immunohistochemical analysis of expressions of hepatic cytochrome P450 in F344 rats following oral treatment with kava extract . Exp. Toxicol. Pathol. , 58 : 223 – 36 .
   PubMed Web of Science ®Google Scholar
• Conney , A. H. , Chang , R. , Levin , W. M. , Garbut , A. , Munro-Faure , A. D. , Peck , A. W. and Bye , A. 1972 . Effects of piperonyl butoxide on drug metabolism in rodents and man . Arch. Environ. Health , 24 : 97 – 106 .
   PubMed Web of Science ®Google Scholar
• Cook , J. C. and Hodgson , E. 1983 . Induction of cytochrome P-450 by methylenedioxyphenyl compounds: Importance of the methylene carbon . Toxicol. Appl. Pharmacol. , 68 : 131 – 39 .
   PubMed Web of Science ®Google Scholar
• Daborn , P. J. , Lumb , C. , Boey , A. , Wong , W. , Ffrench-Constant , R. H. and Batterham , P. 2007 . Evaluating the insecticide resistance potential of eight Drosophila melanogaster cytochrome P450 genes by transgenic over-expression . Insect Biochem. Mol. Biol. , 37 : 512 – 91 .
   PubMed Web of Science ®Google Scholar
• Daborn , P. J. , Yen , J. L. , Bogwitz , M. R. , Le Goff , G. , Feil , E. , Jeffers , S. , Tijet , N. , Perry , T. , Heckel , D. , Batterham , P. , Feyereisen , R. , Wilson , T. G. and Ffrench-Constant , R. H. 2002 . A single P450 allele associated with insecticide resistance . Drosophila. Science , 297 : 2253 – 56 .
   PubMed Web of Science ®Google Scholar
• Denison , M. S. , Fisher , J. M. and Whitlock , J. P. Jr. 1988 . The DNA recognition site for the dioxin-Ah receptor complex. Nucleotide sequence and functional analysis . J. Biol. Chem. , 263 : 17221 – 24 .
   PubMed Web of Science ®Google Scholar
• DeVore , N. M. , Smith , B. D. , Wang , J. L. , Lushington , G. H. and Scott , E. E. 2009 . Key residues controlling binding of diverse ligands to human cytochrome P450 2A enzymes . Drug Metab. Dispos. , 37 : 1319 – 27 .
   PubMed Web of Science ®Google Scholar
• Duangkaew , P. , Pethuan , S. , Kaewpa , D. , Boonsuepsakul , S. , Sarapusit , S. and Rongnoparut , P. 2011 . Characterization of mosquito CYP6P7 and CYP6AA3: Differences in substrate preference and kinetic properties . Arch. Insect Biochem. Physiol. , 76 : 236 – 48 .
   PubMed Web of Science ®Google Scholar
• Dunkov , B. C. , Guzov , V. M. , Mocelin , G. , Shotkoski , F. , Brun , A. , Amichot , M. , Ffrench-Constant , R. H. and Feyereisen , R. 1997 . The Drosophila cytochrome P450 gene Cyp6a2: Structure, localization, heterologous expression, and induction by phenobarbital . DNA Cell Biol. , 16 : 1345 – 56 .
   PubMed Web of Science ®Google Scholar
• Durst , F. and O'Keefe , D. P. 1995 . Plant cytochromes P450: An overview . Drug Metab. Drug Interact. , 12 : 171 – 87 .
   PubMedGoogle Scholar
• Elcombe , C. R. , Bridges , J. W. , Gray , I. J. B. , NimmoSmith , R. H. and Netter , K. J. 1975 . Studies on the interaction of safrole with rat hepatic microsomes . Biochem. Pharmacol. , 24 : 1427 – 33 .
   Web of Science ®Google Scholar
• Farrell , G. C. and Murray , M. 1990 . Human cytochrome P450 isoforms. Their genetic heterogeneity and induction by omeprazole . Gastroenterology , 99 : 885 – 89 .
   PubMed Web of Science ®Google Scholar
• Fennell , T. R. , Sweatman , B. C. and Bridges , J. W. 1980 . The induction of hepatic cytochrome P-450 in C57 BL/10 and DBA/2 mice by isosafrole and piperonyl butoxide. A comparative study with other inducing agents . Chem. Biol. Interact. , 31 : 189 – 201 .
   PubMed Web of Science ®Google Scholar
• Feyereisen , R. 2012 . “ Insect CYP genes and P450 enzymes ” . In Insect molecular biology and biochemistry , Edited by: Gilbert , L. I. 236 – 316 . Waltham, MA: Elsevier .
   Google Scholar
• Feyereisen , R. , Langry , K. C. and Ortiz de Montellano , P. R. 1984 . Self-catalyzed destruction of insect cytochrome P-450 . Insect Biochem. , 14 : 19 – 26 .
   Google Scholar
• Fisher , C. W. and Mayer , R. T. 1982 . Characterization of house fly microsomal mixed function oxidases: Inhibition by juvenile hormone I and piperonyl butoxide . Toxicology , 24 : 15 – 31 .
   PubMed Web of Science ®Google Scholar
• Fisher , G. J. , Fukushima , H. and Gaylor , J. L. 1981 . Isolation, purification, and properties of a unique form of cytochrome P-450 in microsomes of isosafrole-treated rats . J. Biol. Chem. , 256 : 4388 – 94 .
   PubMed Web of Science ®Google Scholar
• Foster , B. C. , Vandenhoek , S. , Hana , J. , Krantis , A. , Akhtar , M. H. , Bryan , M. , Budzinski , J. W. , Ramputh , A. and Arnason , J. T. 2003 . In vitro inhibition of human cytochrome P450-mediated metabolism of marker substrates by natural products . Phytomedicine , 10 : 334 – 42 .
   PubMed Web of Science ®Google Scholar
• Franklin , M. R. 1972a . Inhibition of hepatic oxidative xenobiotic metabolism by piperonyl butoxide . Biochem. Pharmacol. , 21 : 3287 – 99 .
   PubMed Web of Science ®Google Scholar
• Franklin , M. R. 1972b . Piperonyl butoxide metabolism by cytochrome P-450: Factors affecting the formation and disappearance of the metabolite-cytochrome P-450 complex . Xenobiotica , 2 : 517 – 27 .
   PubMed Web of Science ®Google Scholar
• Fu , P. P. , Xia , Q. , Guo , L. , Yu , H. and Chan , P. C. 2008 . Toxicity of kava kava . J. Environ. Sci. Health C Environ. Carcinogen. Ecotoxicol. Rev. , 26 : 89 – 112 .
   PubMed Web of Science ®Google Scholar
• Gersdorf , W. A. , Mitlin , N. and Beroza , M. 1954 . Comparative effects of sesamolin, sesamin, and sesamol in pyrethrum and alethrin mixtures as housefly sprays . J. Econ. Entomol. , 47 : 839 – 842 .
   Web of Science ®Google Scholar
• Gotoh , O. 1992 . Substrate recognition sites in cytochrome P450 family 2 (CYP2) proteins inferred from comparative analyses of amino acid and coding nucleotide sequences . J. Biol. Chem. , 267 : 83 – 90 .
   PubMed Web of Science ®Google Scholar
• Grollman , A. P. , Shibutani , S. , Moriya , M. , Miller , F. , Wu , L. , Moll , U. , Suzuki , N. , Fernandes , A. , Rosenquist , T. , Medverec , Z. , Jakovina , K. , Brdar , B. , Slade , N. , Turesky , R. J. , Goodenough , A. K. , Rieger , R. , Vukelic , M. and Jelakovic , B. 2007 . Aristolochic acid and the etiology of endemic (Balkan) nephropathy . Proc. Natl Acad. Sci. USA , 104 : 12129 – 12134 .
   PubMed Web of Science ®Google Scholar
• Guengerich , F. P. 1990 . Enzymatic oxidation of xenobiotic chemicals . Crit. Rev. Biochem. Mol. Biol. , 25 : 97 – 153 .
   PubMed Web of Science ®Google Scholar
• Guo , L. , Li , Q. , Xia , Q. , Dial , S. , Chan , P. C. and Fu , P. 2009 . Analysis of gene expression changes of drug metabolizing enzymes in the livers of F344 rats following oral treatment with kava extract . Food Chem. Toxicol. , 47 : 433 – 42 .
   PubMed Web of Science ®Google Scholar
• Gurley , B. J. , Gardner , S. F. , Hubbard , M. A. , Williams , D. K. , Gentry , W. B. , Khan , I. A. and Shah , A. 2005 . In vivo effects of goldenseal, kava kava, black cohosh, and valerian on human cytochrome P450 1A2, 2D6, 2E1, and 3A4/5 phenotypes . Clin. Pharmacol. Ther. , 77 : 415 – 26 .
   PubMed Web of Science ®Google Scholar
• Guzov , V. M. , Unnithan , G. C. , Chernogolov , A. A. and Feyereisen , R. 1998 . CYP12A1, a mitochondrial cytochrome P450 from the house fly . Arch. Biochem. Biophys. , 359 : 231 – 40 .
   PubMed Web of Science ®Google Scholar
• Haller , H. L. , La Forge , F. B. and Sullivan , W. N. 1942 . Some compounds related to sesamin: Their structures and their synergistic effect with pyrethrum insecticides . J. Org. Chem. , 7 : 185 – 88 .
   Google Scholar
• Harmatha , J. and Nawrot , J. 2002 . Insect feeding deterrent activity of lignans and related phenylpropanoids with a methylenedioxyphenyl (piperonyl) structure moiety . Entomol. Exp. Appl. , 104 : 51 – 60 .
   Web of Science ®Google Scholar
• Hodgson , E. and Jr , Plapp . 1970 . Biochemical characteristics of insect microsomes . J. Agric. Food Chem. , 18 : 1048 – 55 .
   Web of Science ®Google Scholar
• Hodgson , E. and Philpot , R. M. 1974 . Interaction of methylenedioxyphenyl (1,3-benzodioxole) compounds with enzymes and their effects on mammals . Drug Metab. Rev. , 3 : 231 – 301 .
   PubMed Web of Science ®Google Scholar
• http://drnelson.uthsc.edu/CytochromeP450.html (http://drnelson.uthsc.edu/CytochromeP450.html) (Accessed: 26 March 2010 ).
   Google Scholar
• Humberston , C. L. , Akhtar , J. and Krenzelok , E. P. 2003 . Acute hepatitis induced by kava kava . J. Toxicol. Clin. Toxicol. , 41 : 109 – 13 .
   PubMed Web of Science ®Google Scholar
• Hung , C. F. , Berenbaum , M. R. and Schuler , M. A. 1997 . Isolation and characterization of CYP6B4, a furanocoumarin-inducible cytochrome P450 from a polyphagous caterpillar (Lepidoptera:papilionidae) . Insect Biochem. Mol. Biol. , 27 : 377 – 85 .
   PubMed Web of Science ®Google Scholar
• Imanshahidi , M. and Hosseinzadeh , H. 2008 . Pharmacological and therapeutic effects of Berberis vulgaris and its active constituent, berberine . Phytother. Res. , 22 : 999 – 1012 .
   PubMed Web of Science ®Google Scholar
• Iwata , H. , Tezuka , Y. , Kadota , S. , Hiratsuka , A. and Watabe , T. 2004 . Identification and characterization of potent CYP3A4 inhibitors in Schisandra fruit extract . Drug Metab. Dispos. , 32 : 1351 – 58 .
   PubMed Web of Science ®Google Scholar
• Jelaković , B. , Karanović , S. , Vuković-Lela , I. , Miller , F. , Edwards , K. L. , Nikolić , J. , Tomić , K. , Slade , N. , Brdar , B. , Turesky , R. J. , Stipančić , Z. , Dittrich , D. , Grollman , A. P. and Dickman , K. G. 2012 . Aristolactam-DNA adducts are a biomarker of environmental exposure to aristolochic acid . Kidney Int. , 81 : 559 – 67 .
   PubMed Web of Science ®Google Scholar
• Jenner , G. , Nahmed , E. M. and Leismann , H. 1990 . Homogeneous activation of the C-H bond in formates. Decarbonylation of formates to alcohols . J. Organomet. Chem. , 387 : 315 – 21 .
   Web of Science ®Google Scholar
• Jensen , H. R. , Scott , I. M. , Sims , S. R. , Trudeau , V. L. and Arnason , J. T. 2006 . The effect of a synergistic concentration of a Piper nigrum extract used in conjunction with pyrethrum upon gene expression . Drosophila melanogaster. Insect Mol. Biol. , 15 : 329 – 39 .
   PubMed Web of Science ®Google Scholar
• Jeurissen , S. M. , Bogaards , J. J. , Awad , H. M. , Boersma , M. G. , Brand , W. , Fiamegos , Y. C. , van Beek , T. A. , Alink , G. M. , Sudholter , E. J. , Cnubben , N. H. and Rietjens , I. M. 2004 . Human cytochrome P450 enzyme specificity for bioactivation of safrole to the proximate carcinogen 1'-hydroxysafrole . Chem. Res. Toxicol. , 17 : 1245 – 50 .
   PubMed Web of Science ®Google Scholar
• Johnson , B. M. , Qiu , S. X. , Zhang , S. , Zhang , F. , Burdette , J. E. , Yu , L. , Bolton , J. L. and van Breemen , R. B. 2003 . Identification of novel electrophilic metabolites of Piper methysticum Forst (Kava) . Chem. Res. Toxicol. , 16 : 733 – 40 .
   PubMed Web of Science ®Google Scholar
• Jones , R. T. , Bakker , S. E. , Stone , D. , Shuttleworth , S. N. , Boundy , S. , McCart , C. , Daborn , P. J. , Ffrench-Constant , R. H. and van den Elsen , J. M. 2010 . Homology modelling of Drosophila cytochrome P450 enzymes associated with insecticide resistance . Pestic. Manage. Sci. , 66 : 1106 – 15 .
   PubMed Web of Science ®Google Scholar
• Kang , M. H. , Won , S. M. , Park , S. S. , Kim , S. G. , Novak , R. F. and Kim , N. D. 1994 . Piperine effects on the expression of P4502E1, P4502B and P4501A in rat . Xenobiotica , 24 : 1195 – 204 .
   PubMed Web of Science ®Google Scholar
• Kao , L. R. and Wilkinson , C. F. 1987 . Inhibition of cytochrome P-450c-mediated benzo[a]pyrene hydroxylase and ethoxyresorufin O-deethylase by dihydrosafrole . Xenobiotica , 17 : 793 – 805 .
   PubMed Web of Science ®Google Scholar
• Karunker , I. , Benting , J. , Lueke , B. , Ponge , T. , Nauen , R. , Roditakis , E. , Vontas , J. , Gorman , K. , Denholm , I. and Morin , S. 2008 . Over-expression of cytochrome P450 CYP6CM1 is associated with high resistance to imidacloprid in the B and Q biotypes of Bemisia tabaci (Hemiptera: Aleyrodidae) . Insect Biochem. Mol. Biol. , 38 : 634 – 44 .
   PubMed Web of Science ®Google Scholar
• Kasai , S. and Scott , J. G. 2000 . Over-expression of cytochrome P450 CYP6D1 in pyrethroid resistant strains of house fly from North America . Pestic. Biochem. Physiol. , 68 : 34 – 41 .
   Web of Science ®Google Scholar
• King-Jones , K. , Horner , M. A. , Lam , G. and Thummel , C. S. 2006 . The DHR96 nuclear receptor regulates xenobiotic responses . Drosophila. Cell Metab. , 4 : 37 – 48 .
   PubMed Web of Science ®Google Scholar
• Kumagai , Y. , Fukuto , J. M. and Cho , A. K. 1994 . The biochemical disposition of methylenedioxyphenyl compounds . Curr. Med. Chem. , 1 : 254 – 61 .
   Google Scholar
• Lajide , L. , Escoubas , P. and Mizutani , J. 1993 . Comparative effects of aristolochic acids, phenanthrene, and 1,3-benzodioxole derivatives on the behavior and survival of Spodoptera litura larvae . J. Agric. Food Chem. , 41 : 2426 – 30 .
   Web of Science ®Google Scholar
• Lee , J. M. , Liu , T. Y. , Wu , D. C. , Tang , H. C. , Leh , J. , Wu , M. T. , Hsu , H. H. , Huang , P. M. , Chen , J. S. , Lee , C. J. and Lee , Y. C. 2005 . Safrole–DNA adducts in tissues from esophageal cancer patients: clues to areca-related esophageal carcinogenesis . Mutat. Res. , 565 : 121 – 28 .
   PubMed Web of Science ®Google Scholar
• Lewandowski , M. , Chui , Y. C. , Levi , P. E. and Hodgson , E. 1990 . Differences in induction of hepatic cytochrome P450 isozymes by mice in eight methylenedioxyphenyl compounds . J. Biochem. Toxicol. , 5 : 47 – 55 .
   PubMedGoogle Scholar
• Lewis , D. F. and Ito , Y. 2010 . Human CYPs involved in drug metabolism: structures, substrates and binding affinities . Expert Opin. Drug Metab. Toxicol. , 6 : 661 – 74 .
   PubMed Web of Science ®Google Scholar
• Li , X. , Baudry , J. , Berenbaum , M. R. and Schuler , M. A. 2004 . Structural and functional divergence of insect CYP6B proteins: From specialist to generalist cytochrome P450 . Proc. Natl. Acad. Sci. USA , 101 : 2939 – 44 .
   PubMed Web of Science ®Google Scholar
• Li , Y. , Mei , H. , Wu , Q. , Zhang , S. , Fang , J. L. , Shi , L. and Guo , L. 2011 . Methysticin and 7,8-dihydromethysticin are two major kavalactones in kava extract to induce CYP1A1 . Toxicol. Sci. , 124 : 388 – 99 .
   PubMed Web of Science ®Google Scholar
• Lichtenstein , E. P. and Casida , J. E. 1963 . Myristicin, an insecticide and synergist occurring naturally in the edible parts of parsnips . J. Agric. Food Chem. , 11 : 410 – 15 .
   Web of Science ®Google Scholar
• Lin , G. G. , Kozaki , T. and Scott , J. G. 2011 . Hormone receptor-like in 96 and Broad-Complex modulate phenobarbital induced transcription of cytochrome P450 CYP6D1 in Drosophila S2 cells . Insect Mol. Biol. , 20 : 87 – 95 .
   PubMed Web of Science ®Google Scholar
• Liu , T. Y. , Chen , C. C. , Chen , C. L. and Chi , C. W. 1999 . Safrole-induced oxidative damage in the liver of Sprague-Dawley rats . Food Chem. Toxicol. , 37 : 697 – 702 .
   PubMed Web of Science ®Google Scholar
• Ma , R. , Cohen , M. B. , Berenbaum , M. R. and Schuler , M. A. 1994 . Black swallowtail (Papilio polyxenes) alleles encode cytochrome P450s that selectively metabolize linear furanocoumarins . Arch. Biochem. Biophys. , 310 : 332 – 40 .
   PubMed Web of Science ®Google Scholar
• Ma , Y. , Sachdeva , K. , Liu , J. , Ford , M. , Yang , D. , Khan , I. A. , Chichester , C. O. and Yan , B. 2004 . Desmethoxyyangonin and dihydromethysticin are two major pharmacological kavalactones with marked activity on the induction of CYP3A23 . Drug Metab. Dispos. , 32 : 1317 – 24 .
   PubMed Web of Science ®Google Scholar
• Maitra , S. , Dombrowski , S. M. , Waters , L. C. and Ganguly , R. 1996 . Three second chromosome-linked clustered Cyp6 genes show differential constitutive and barbital-induced expression in DDT-resistant and susceptible strains of . Drosophila melanogaster. Gene , 180 : 165 – 71 .
   Google Scholar
• Mangelsdorf , D. J. , Thummel , C. , Beato , M. , Herrlich , P. , Schütz , G. , Umesono , K. , Blumberg , B. , Kastner , P. , Mark , M. , Chambon , P. and Evans , R. M. 1995 . The nuclear receptor superfamily: The second decade . Cell , 83 : 835 – 39 .
   PubMed Web of Science ®Google Scholar
• Mansuy , D. , Battioni , J. P. , Chottard , J. C. and Ullrich , V. 1979 . Preparation of a porphyrin iron carbene model for cytochrome P-450 complexes obtained upon metabolic activation of the insecticide synergists of the 1,3-benzodioxole series . J. Am. Chem. Soc. , 101 : 3971 – 72 .
   Web of Science ®Google Scholar
• Mantena , S. K. , Sharma , S. D. and Katiyar , S. K. 2006 . Berberine, a natural product, induces G1-phase cell cycle arrest and caspase-3-dependent apoptosis in human prostate carcinoma cells . Mol. Cancer Ther. , 5 : 296 – 308 .
   PubMed Web of Science ®Google Scholar
• Mao , W. , Zangerl , A. R. , Berenbaum , M. R. and Schuler , M. A. 2008 . Metabolism of myristicin by Depressaria pastinacella CYP6AB3v2 and inhibition by its metabolite . Insect Biochem. Mol. Biol. , 38 : 645 – 51 .
   PubMed Web of Science ®Google Scholar
• Mao , W. , Schuler , M. A. and Berenbaum , M. R. 2007a . Cytochrome P450s in Papilio multicaudatus and the transition from oligophagy to polyphagy in the Papilionidae . Insect Mol. Biol. , 16 : 481 – 90 .
   PubMed Web of Science ®Google Scholar
• Mao , W. , Rupasinghe , S. G. , Zangerl , A. R. , Berenbaum , M. R. and Schuler , M. A. 2007b . Allelic variation in the Depressaria pastinacella CYP6AB3 protein enhances metabolism of plant allelochemicals by altering a proximal surface residue and potential interactions with cytochrome P450 reductase . J. Biol. Chem. , 282 : 10544 – 52 .
   PubMed Web of Science ®Google Scholar
• Mao , W. , Rupasinghe , S. G. , Johnson , R. M. , Zangerl , A. R. , Schuler , M. A. and Berenbaum , M. R. 2009 . Quercetin-metabolizing CYP6AS enzymes of the pollinator Apis mellifera (Hymenoptera: Apidae) . Comp. Biochem. Physiol. B , 154 : 427 – 34 .
   PubMed Web of Science ®Google Scholar
• Mao , W. , Rupasinghe , S. , Zangerl , A. R. , Schuler , M. A. and Berenbaum , M. R. 2006 . Remarkable substrate-specificity of CYP6AB3 in Depressaria pastinacella, a highly specialized caterpillar . Insect Mol. Biol. , 15 : 169 – 79 .
   PubMed Web of Science ®Google Scholar
• Marcus , C. B. , Murray , M. and Wilkinson , C. F. 1985 . Spectral and inhibitory interactions of methylenedioxyphenyl and related compounds with purified isozymes of cytochrome P-450 . Xenobiotica , 15 : 351 – 62 .
   PubMed Web of Science ®Google Scholar
• Marcus , C. B. , Murray , M. , Wang , C. and Wilkinson , C. F. 1986 . Methylenedioxyphenyl compounds as inducers of cytochrome P-450 and monooxygenase activity in the Southern armyworm (Spodoptera eridania) and the rat . Pest. Biochem. Physiol. , 26 : 310 – 22 .
   Web of Science ®Google Scholar
• Marcus , C. B. , Murray , M. , Hetnarski , K. and Wilkinson , C. F. 1987 . Methylenedioxyphenyl complexes with microsomal cytochrome P-450: In vivo complex formation in rat liver and in midgut tissues of the Southern armyworm (Spodoptera eridania) . Pest. Biochem. Physiol. , 28 : 140 – 47 .
   Web of Science ®Google Scholar
• Marcus , C. B. , Wilson , N. M. , Jefcoate , C. R. , Wilkinson , C. F. and Omiecinski , C. J. 1990 . Selective induction of cytochrome P450 isozymes in rat liver by 4-n-alkyl-methylenedioxybenzenes . Arch. Biochem. Biophys. , 277 : 8 – 16 .
   PubMed Web of Science ®Google Scholar
• Martati , E. , Boersma , M. G. , Spenkelink , A. , Khadka , D. B. , Punt , A. , Vervoort , J. , van Bladeren , P. J. and Rietjens , I. M. 2011 . Physiologically based biokinetic (PBBK) model for safrole bioactivation and detoxification in rats . Chem. Res. Toxicol. , 24 : 818 – 34 .
   PubMed Web of Science ®Google Scholar
• Mathews , J. M. , Etheridge , A. S. and Black , S. R. 2002 . Inhibition of human cytochrome P450 activities by kava extract and kavalactones . Drug Metab. Dispos. , 30 : 1153 – 57 .
   PubMed Web of Science ®Google Scholar
• Matthews , H. B. , Skrinjarić-Spoljar , M. and Casida , J. E. 1970 . Insecticide synergist interactions with cytochrome P-450 in mouse liver microsomes . Life Sci. , 9 : 1039 – 48 .
   Web of Science ®Google Scholar
• Mayer , R. T. , Fisher , C. W. , Cocke , J. , Bridges , A. C. and Olson , J. K. 1982 . Studies on a fluorescent insect growth regulator metabolite complex with house-fly microsomal cytochrome P-450 . Pest. Biochem. Physiol. , 17 : 24 – 34 .
   Web of Science ®Google Scholar
• McDonnell , C. M. , Brown , R. P. , Berenbaum , M. R. and Schule , M. A.. 2004 . Conserved regulatory elements in the promoters of two allelochemical-inducible cytochrome P450 genes differentially regulate transcription . Insect Biochem. Mol. Biol. , 34 : 1129 – 39 .
   PubMed Web of Science ®Google Scholar
• McLaughlin , L. A. , Niazi , U. , Bibby , J. , David , J. P. , Vontas , J. , Hemingway , J. , Ranson , H. , Sutcliffe , M. J. and Paine , M. J. 2008 . Characterization of inhibitors and substrates of Anopheles gambiae CYP6Z2 . Insect Mol. Biol. , 17 : 125 – 35 .
   PubMed Web of Science ®Google Scholar
• Miller , J. S. and Feeny , P. 1989 . Interspecific differences among swallowtail larvae (Lepidoptera: Papilionidae) in susceptibility to aristolochic acids and berberine . Ecol. Entomol. , 14 : 287 – 96 .
   Web of Science ®Google Scholar
• Murray , M. 1991 . In vitro and in vivo studies of the effect of vitamin E on microsomal cytochrome P450 in rat liver . Biochem. Pharmacol. , 42 : 2107 – 14 .
   PubMed Web of Science ®Google Scholar
• Murray , M. 2000 . Mechanisms of inhibitory and regulatory effects of methylenedioxyphenyl compounds on cytochrome P450-dependent drug oxidation . Curr. Drug Metab. , 1 : 67 – 84 .
   PubMed Web of Science ®Google Scholar
• Murray , M. 2006 . Altered CYP expression and function in response to dietary factors: potential roles in disease pathogenesis . Curr. Drug. Metab. , 7 : 67 – 81 .
   PubMed Web of Science ®Google Scholar
• Murray , M. and Reidy , G. F. 1990 . Selectivity in the inhibition of mammalian cytochromes P-450 by chemical agents . Pharmacol. Rev. , 42 : 85 – 101 .
   PubMed Web of Science ®Google Scholar
• Murray , M. , Marcus , C. B. and Wilkinson , C. F. 1985a . Quantitative structure–activity relationships in the displacement of the dihydrosafrole metabolite-cytochrome P-450 complex . Quant. Struct. Activity Relat. , 4 : 18 – 22 .
   Google Scholar
• Murray , M. , Wilkinson , C. F. and Dube , C. E. 1983a . Effects of dihydrosafrole on cytochrome P-450 and drug oxidation in hepatic microsomes from control and induced rats . Toxicol. Appl. Pharmacol. , 68 : 66 – 76 .
   PubMed Web of Science ®Google Scholar
• Murray , M. , Wilkinson , C. F. and Dube , C. E. 1985b . Induction of rat-hepatic microsomal cytochrome P-450 and aryl hydrocarbon hydroxylase by 1,3-benzodioxole derivatives . Xenobiotica , 15 : 361 – 68 .
   PubMed Web of Science ®Google Scholar
• Murray , M. , Wilkinson , C. F. , Marcus , C. B. and Dube , C. E. 1983b . Structure–activity relationships in the interactions of alkoxymethylenedioxybenzene derivatives with rat hepatic microsomal mixedfunction oxidases . in vivo. Mol. Pharmacol. , 24 : 129 – 36 .
   PubMed Web of Science ®Google Scholar
• Murray , M. , Zaluzny , L. and Farrell , G. C. 1986 . Selective reactivation of steroid hydroxylases following dissociation of the isosafrole metabolite complex with rat hepatic cytochrome P-450 . Arch. Biochem. Biophys. , 251 : 471 – 78 .
   PubMed Web of Science ®Google Scholar
• Nakajima , M. , Suzuki , M. , Yamaji , R. , Takashina , H. , Shimada , N. , Yamazaki , H. and Yoko , T. 1999 . Isoform selective inhibition and inactivation of human cytochrome P450s by methylenedioxyphenyl compounds . Xenobiotica , 29 : 1191 – 202 .
   PubMed Web of Science ®Google Scholar
• Navickiene , H. M. , Miranda , J. E. , Bortoli , S. A. , Kato , M. J. , Bolzani , V. S. and Furlan , M. 2007 . Toxicity of extracts and isobutyl amides from Piper tuberculatum: Potent compounds with potential for the control of the velvetbean caterpillar . Anticarsia gemmatalis. Pest. Manage. Sci. , 63 : 399 – 403 .
   PubMed Web of Science ®Google Scholar
• Nawrot , J. , Koul , O. , Isman , M. B. and Harmatha , J. 1991 . Naturally occurring antifeedants: Effects on two polyphagous lepidopterans . J. Appl. Entomol. , 112 : 194 – 201 .
   Web of Science ®Google Scholar
• Neal , J. J. 1989 . Methylenedioxyphenyl-containing alkaloids and autosynergism . Phytochemistry , 28 : 451 – 53 .
   Web of Science ®Google Scholar
• Neal , J. J. and Berenbaum , M. R. 1989 . Decreased sensitivity of mixed-function oxidases from papilio polyxenes to inhibitors in host plants . J. Chem. Ecol. , 15 : 439 – 46 .
   PubMed Web of Science ®Google Scholar
• Nelson , D. and Werck-Reichhart , D. 2011 . A P450-centric view of plant evolution . Plant J. , 66 : 194 – 211 .
   PubMed Web of Science ®Google Scholar
• Niu , G. , When , Z. , Rupasinghe , S. G. , Zeng , R. S. , Berenbaum , M. R. and Schuler , M. A. 2008 . Aflatoxin B1 detoxification by CYP321A1 in Helicoverpa zea . Arch. Insect Biochem. Physiol. , 69 : 32 – 45 .
   PubMed Web of Science ®Google Scholar
• Niu , G. , Rupasinghe , S. G. , Zangerl , A. R. , Siegel , J. P. , Schuler , M. A. and Berenbaum , M. R. 2011 . A substrate-specific cytochrome P450 monooxygenase, CYP6AB11, from the polyphagous navel orangeworm (Amyelois transitella) . Insect Biochem. Mol Biol. , 41 : 244 – 53 .
   PubMed Web of Science ®Google Scholar
• Ortiz de Montellano , P. R. 1995 . “ Oxygen activation and reactivity ” . In Cytochrome P450: Structure, mechanism and biochemistry , 2nd , Edited by: Ortiz de Montellano , P. R. 245 – 302 . New York , NY : Plenum Press .
   Google Scholar
• Park , I. K. , Shin , S. C. , Kim , C. S. , Lee , H. J. , Choi , W. S. and Ahn , Y. J. 2005 . Larvicidal activity of lignans identified in Phryma leptostachya Var. asiatica roots against three mosquito species . J. Agric. Food Chem. , 53 : 969 – 72 .
   PubMed Web of Science ®Google Scholar
• Parker , R. S. , Sontag , T. J. and Swanson , J. E. 2000 . Cytochrome P4503A-dependent metabolism of tocopherols and inhibition by sesamin . Biochem. Biophys. Res. Commun. , 277 : 531 – 34 .
   PubMed Web of Science ®Google Scholar
• Perry , A. S. and Buckner , A. J. 1970 . Studies on microsomal cytochrome P-450 in resistant and susceptible house flies . Life Sci. , 9 : 335 – 50 .
   PubMed Web of Science ®Google Scholar
• Perry , A. S. and Hoskins , W. M. 1951 . Synergistic action with DDT toward resistant house flies . J. Econ. Entomol. , 44 : 839 – 50 .
   Web of Science ®Google Scholar
• Petersen , R. A. , Niamsup , H. , Berenbaum , M. R. and Schuler , M. A. 2003 . Transcriptional response elements in the promoter of CYP6B1, an insect P450 gene regulated by plant chemicals . Biochim. Biophys. Acta , 1619 : 269 – 82 .
   PubMed Web of Science ®Google Scholar
• Phukan , R. K. , Ali , M. S. , Chetia , C. K. and Mahanta , J. 2001 . Betel nut and tobacco chewing; potential risk factors of cancer of oesophagus in Assam, India . Br. J. Cancer , 85 : 661 – 67 .
   PubMed Web of Science ®Google Scholar
• Pittler , M. H. and Ernst , E. 2003 . Kava extract for treating anxiety . Cochrane Database Syst. Rev. , 1 : CD003383
   Google Scholar
• Porro , C. S. , Sutcliffe , M. J. and de Visser , S. P. 2009 . Quantum mechanics/molecular mechanics studies on the sulfoxidation of dimethyl sulfide by compound I and compound 0 of cytochrome P450: Which is the better oxidant? . J. Phys. Chem. A. , 113 : 11635 – 42 .
   PubMed Web of Science ®Google Scholar
• Ranasinghe , C. , Campbell , B. and Hobbs , A. A. 1998 . Over-expression of cytochrome P450 CYP6B7 mRNA and pyrethroid resistance in Australian populations of Helicoverpa armigera (Hubner) . Pestic. Sci. , 54 : 195 – 202 .
   Google Scholar
• Raucy , J. L. 2003 . Regulation of CYP3A4 expression in human hepatocytes by pharmaceuticals and natural products . Drug Metab. Dispos. , 31 : 533 – 39 .
   PubMed Web of Science ®Google Scholar
• Russmann , S. , Lauterburg , B. H. and Helbling , A. 2001 . Kava hepatotoxicity . Ann. Intern. Med. , 135 : 68 – 69 .
   PubMed Web of Science ®Google Scholar
• Ryan , D. E. , Thomas , P. E. and Levin , W. 1980 . Hepatic microsomal cytochrome P-450 from rats treated with isosafrole. Purification and characterization of four enzymic forms . J. Biol. Chem. , 255 : 7941 – 55 .
   PubMed Web of Science ®Google Scholar
• Ryu , D. Y. , Levi , P. E. and Hodgson , E. 1995 . Regulation of cytochrome P-450 isozymes CYP1A1, CYP1A2 and CYP2B10 by three benzodioxole compounds . Chem. -Biol. Interact. , 96 : 235 – 47 .
   PubMed Web of Science ®Google Scholar
• Ryu , D. Y. , Levi , P. E. , Fernandez-Salguero , P. , Gonzalez , F. J. and Hodgson , E. 1996 . Piperonyl butoxide and acenaphthylene induce cytochrome P450 1A2 and 1B1 mRNA in aromatic hydrocarbon-responsive receptor knock-out mouse liver . Mol Pharmacol. , 50 : 443 – 46 .
   PubMed Web of Science ®Google Scholar
• Sabourault , C. , Guzov , V. M. , Koener , J. F. , Claudianos , C. , Plapp , F. W. Jr. and Feyereisen , R. 2001 . Overproduction of a P450 that metabolizes diazinon is linked to a loss- of-function in the chromosome 2 ali-esterase (MdalphaE7) gene in resistant house flies . Insect Mol. Biol. , 10 : 609 – 18 .
   PubMed Web of Science ®Google Scholar
• Saner , C. , Weibel , B. , Wurgler , F. E. and Sengstag , C. 1996 . Metabolism of promutagens catalyzed by Drosophila melanogaster CYP6A2 enzyme in Saccharomyces . cerevisiae. Environ. Mol. Mutagen. , 27 : 46 – 58 .
   PubMed Web of Science ®Google Scholar
• Sasabe , M. , Wen , Z. , Berenbaum , M. R. and Schuler , M. A. 2004 . Molecular analysis of CYP321A1, a novel cytochrome P450 involved in metabolism of plant allelochemicals (furanocoumarins) and insecticides (cypermethrin) . Helicoverpa zea. Gene , 338 : 163 – 75 .
   Google Scholar
• Schmeiser , H. H. , Bieler , C. A. , Wiessler , M. , van Ypersele de Strihou , C. and Cosyns , J. P. 1996 . Detection of DNA adducts formed by aristolochic acid in renal tissue from patients with Chinese herbs nephropathy . Cancer Res. , 56 : 2025 – 28 .
   PubMed Web of Science ®Google Scholar
• Schmeiser , H. H. , Janssen , J. W. , Lyons , J. , Scherf , H. R. , Pfau , W. , Buchmann , A. , Bartram , C. R. and Wiessler , M. 1990 . Aristolochic acid activates ras genes in rat tumors at deoxyadenosine residues . Cancer Res. , 50 : 5464 – 69 .
   PubMed Web of Science ®Google Scholar
• Schonbrod , R. D. , Khan , M. A. Q. , Terriere , L. C. and Plapp , F. W. 1968 . Microsomal oxidase in the housefly: A survey of fourteen strains . Life Sci. , 7 : 681 – 88 .
   Web of Science ®Google Scholar
• Schuler , M. A. 2011 . P450s in plant-insect interactions . Biochim. Biophys. Acta , 1814 : 36 – 45 .
   PubMed Web of Science ®Google Scholar
• Scott , I. M. , Jensen , H. R. , Philogène , B. J. R. and Arnason , J. T. 2008 . A review of Piper spp. (Piperaceae) phytochemistry, insecticidal activity and mode of action . Phytochem. Rev. , 7 : 65 – 75 .
   Google Scholar
• Scott , J. G. , Foroozesh , M. , Hopkins , N. E. , Alefantis , T. G. and Alworth , W. L. 2000 . Inhibition of cytochrome P450 6D1 by alkynylarenes, methylenedioxyarenes, and other substituted aromatics . Pestic. Biochem. Physiol. , 67 : 63 – 71 .
   Web of Science ®Google Scholar
• Scriber , J. M. , Lederhouse , R. C. and Hagen , R. H. 1991 . “ Foodplants and evolution within Papilio glaucus and Papilio troilus species groups (Lepidoptera: Papilionidae) ” . In Plant–animal interactions: Evolutionary ecology in tropical and temperate regions , Edited by: Price , P. W. , Lewinsohn , T. M. , Fernandes , G. W. and Benson , W. W. 341 – 373 . New York , NY : John Wiley and Sons .
   Google Scholar
• Sidhu , J. S. , Marcus , C. B. , Parkinson , A. and Omiecinski , C. J. 1998 . Differential induction of cytochrome P450 gene expression by 4-n-alkyl-methylenedioxybenzenes in primary rat hepatocyte cultures . J. Biochem. Mol. Toxicol. , 12 : 253 – 62 .
   PubMed Web of Science ®Google Scholar
• Stevenson , B. J. , Bibby , J. , Pignatelli , P. , Muangnoicharoen , S. , O'Neill , P. M. , Lian , L. Y. , Muller , P. , Nikou , D. , Steven , A. , Hemingway , J. , Sutcliffe , M. J. and Paine , M. J. 2011 . Cytochrome P450 6M2 from the malaria vector Anopheles gambiae metabolizes pyrethroids: Sequential metabolism of deltamethrin revealed . Insect Biochem. Mol. Biol. , 41 : 492 – 502 .
   PubMed Web of Science ®Google Scholar
• Stevenson , B. J. , Pignatelli , P. , Nikou , D. and Paine , M. J. I. 2012 . Pinpointing P450s associated with pyrethroid metabolism in the dengue vector, Aedes aegypti: Developing new tools to combat insecticide resistance . PLoS Negl. Trop. Dis. , 6 : e1595
   Web of Science ®Google Scholar
• Steward , A. R. , Wrighton , S. A. , Pasco , D. S. , Fagan , J. B. , Li , D. and Guzelian , P. S. 1985 . Synthesis and degradation of 3-methylcholanthrene-inducible cytochromes P-450 and their mRNAs in primary monolayer cultures of adult rat hepatocytes . Arch. Biochem. Biophys. , 241 : 494 – 508 .
   PubMed Web of Science ®Google Scholar
• Stiborová , M. , Frei , E. , Arlt , V. M. and Schmeiser , H. H. 2008 . Metabolic activation of carcinogenic aristolochic acid, a risk factor for Balkan endemic nephropathy . Mutat. Res , 658 : 55 – 67 .
   PubMed Web of Science ®Google Scholar
• Stiborová , M. , Levová , K. , Bárta , F. , Shi , Z. , Frei , E. , Schmeiser , H. H. , Nebert , D. W. , Phillips , D. H. and Arlt , V. M. 2012 . Bioactivation versus detoxication of the urothelial carcinogen aristolochic acid I by human cytochrome P450 1A1 and 1A2 . Toxicol. Sci. , 125 : 345 – 58 .
   PubMed Web of Science ®Google Scholar
• Sun , W. , Margrn , V. M. , Sun , L. , Buczkowski , G. , Bennet , G. W. , Schemerhorn , B. , Muir , W. M. and Pittendrigh , B. R. 2006 . Genome-wide analysis of phenobarbital-inducible genes . Drosophila melanogaster. Insect Mol. Biol. , 15 : 455 – 64 .
   PubMed Web of Science ®Google Scholar
• Sun , Y. P. and Johnson , E. R. 1960 . Synergistic and antagonistic actions of insecticide–synergist combinations and their mode of action . J. Agric. Food Chem. , 8 : 261 – 66 .
   Web of Science ®Google Scholar
• Szklarz , G. D. and Halpert , J. R. 1998 . Molecular basis of P450 inhibition and activation: implications for drug development and drug therapy . Drug Metab. Dispos. , 26 : 1179 – 84 .
   PubMed Web of Science ®Google Scholar
• Taylor , J. M. , Jenner , P. M. and Jones , W. I. . 1964 . A comparison of the toxicity of some allyl, propenyl, and propyl compounds in the rat . Toxicol. Appl. Pharmacol. , 6 : 378 – 87 .
   PubMed Web of Science ®Google Scholar
• Teschke , R. , Gaus , W. and Loew , D. 2003 . Kava extracts: Safety and risks including rare hepatotoxicity . Phytomedicine , 10 : 440 – 46 .
   PubMed Web of Science ®Google Scholar
• Thongsinthueak , T. C. and Krieger , R. I. 1974 . Inhibitory and inductive effects of piperonyl butoxide on dihydroisodrin hydroxylation in vivo and in vitro in black cutworm (Agrotis ypsilon) larvae . Life Sci. , 14 : 2131 – 41 .
   PubMed Web of Science ®Google Scholar
• Tsai , R. S. , Carrupt , P. A. , Testa , B. and Caldwell , J. 1994 . Structure-genotoxicity relationships of allylbenzenes and propenylbenzenes: A quantum chemical study . Chem. Res. Toxicol. , 7 : 73 – 76 .
   PubMed Web of Science ®Google Scholar
• Ueng , Y.-F. , Hsieh , C.-H. and Don , M.-J. 2005 . Inhibition of human cytochrome P450 enzymes by the natural hepatotoxin safrole . Food Chem. Toxicol. , 43 : 707 – 12 .
   PubMed Web of Science ®Google Scholar
• Ueng , Y.-F. , Hsieh , C.-H. , Don , M.-J. and Ho , L.-K. 2004 . Identification of the main cytochrome P450 enzymes involved in safrole 1′-hydroxylation . Chem. Res. Toxicol. , 17 : 1151 – 56 .
   PubMed Web of Science ®Google Scholar
• Usia , T. , Watabe , T. , Kadota , S. and Tezuka , Y. 2005a . Metabolite–cytochrome P450 complex formation by methylenedioxyphenyl lignans of Piper cubeba: Mechanism-based inhibition . Life Sci. , 76 : 2381 – 91 .
   PubMed Web of Science ®Google Scholar
• Usia , T. , Watabe , T. , Kadota , S. and Tezuka , Y. 2005b . Potent CYP3A4 inhibitory constituents of . Piper cubeba. J. Nat. Prod. , 68 : 64 – 68 .
   PubMed Web of Science ®Google Scholar
• Vanherweghem , J.-L. , Tielemans , C. , Abramowicz , D. , Depierreux , M. , Vanhaelen-Fastre , R. , Vanhaelen , M. , Dratwa , M. , Richard , C. , Vandervelde , D. , Verbeelen , D. and Jadoul , M. 1993 . Rapidly progressive interstitial renal fibrosis in young women: Association with slimming regimen including Chinese herbs . Lancet , 341 : 387 – 91 .
   PubMed Web of Science ®Google Scholar
• Voorman , R. and Aust , S. D. 1988 . Inducers of cytochrome P-450d: Influence on microsomal catalytic activities and differential regulation by enzyme stabilization . Arch. Biochem. Biophys. , 262 : 76 – 84 .
   PubMed Web of Science ®Google Scholar
• Wang , X. P. and Hobbs , A. A. 1995 . Isolation and sequence analysis of a cDNA clone for a pyrethroid inducible cytochrome P450 from . Helicoverpa armigera. Insect Biochem. Mol. Biol. , 25 : 1001 – 9 .
   PubMed Web of Science ®Google Scholar
• Waxman , D. J. , Dannan , G. A. and Guengerich , F. P. 1985 . Regulation of rat hepatic cytochrome P-450: Age-dependent expression, hormonal imprinting, and xenobiotic inducibility of sex-specific isoenzymes . Biochemistry , 24 : 4409 – 17 .
   PubMed Web of Science ®Google Scholar
• Wen , Z. , Rupasinghe , S. , Niu , G. , Berenbaum , M. R. and Schuler , M. A. 2006a . CYP6B1 and CYP6B3 of the black swallowtail (Papilio polyxenes): Adaptive evolution through subfunctionalization . Mol. Biol. Evol. , 23 : 2434 – 43 .
   PubMed Web of Science ®Google Scholar
• Wen , Z. , Pan , L. , Berenbaum , M. R. and Schuler , M. A. 2003 . Metabolism of linear and angular furanocoumarins by Papilio polyxenes CYP6B1 co-expressed with NADPH cytochrome P450 reductase . Insect Biochem. Mol. Biol. , 33 : 937 – 47 .
   PubMed Web of Science ®Google Scholar
• Wen , Z. , Berenbaum , M. R. and Schuler , M. A. 2006b . Inhibition of CYP6B1-mediated detoxification of xanthotoxin by plant allelochemicals in the black swallowtail (Papilio polyxenes) . J. Chem. Ecol. , 32 : 507 – 22 .
   PubMed Web of Science ®Google Scholar
• Wilkinson , C. F. , Metcalf , R. L. and Fukuto , T. R. 1966 . Some structural requirements of methylenedioxyphenyl derivatives as synergists of carbamate insecticides . J. Agric. Food Chem. , 14 : 73 – 79 .
   Web of Science ®Google Scholar
• Wislocki , P. G. , Borchert , P. , Miller , J. A. and Miller , E. C. 1976 . The metabolic activation of the carcinogen 1'-hydroxysafrole in vivo and in vitro and the electrophilic reactivities of possible ultimate carcinogens . Cancer Res. , 36 : 1686 – 95 .
   PubMed Web of Science ®Google Scholar
• Wu , M. T. , Lee , Y. C. , Chen , C. J. , Yang , P. W. , Lee , C. J. , Wu , D. C. , Hsu , H. K. , Ho , C. K. , Kao , E. L. and Lee , J. M. 2001 . Risk of betel chewing for oesophageal cancer in Taiwan . Br. J. Cancer , 85 : 658 – 60 .
   PubMed Web of Science ®Google Scholar
• Yamauchi , S. and Taniguchi , E. 1992a . Synthesis and insecticidal activity of lignan analogs. III . Biosci. Biotechnol. Biochem. , 56 : 418 – 22 .
   PubMed Web of Science ®Google Scholar
• Yamauchi , S. and Taniguchi , E. 1992b . Synthesis and insecticidal activity of sesquilignan analogs with 2-alkyl-6-methoxy-3-(3,4-methylenedioxyphenyl)-1,4-benzodioxanyl group . Biosci. Biotechnol. Biochem. , 56 : 1751 – 59 .
   PubMed Web of Science ®Google Scholar
• Yang , M.-S. , Chung , T.-C. , Yang , M.-J. , Hsu , T.-Y. and Ko , Y.-C. 2001 . betel quid chewing and risk of adverse birth outcomes among aborigines in eastern Taiwan . J. Toxicol. Environ. Health A. , 64 : 465 – 72 .
   PubMed Web of Science ®Google Scholar
• Yasuda , K. , Ikushiro , S. , Kamakura , M. , Ohta , M. and Sakaki , T. 2010 . Metabolism of sesamin by cytochrome P450 in human liver microsomes . Drug Metab. Dispos. , 38 : 2117 – 23 .
   PubMed Web of Science ®Google Scholar
• Yoo , H. H. , Lee , S. H. , Jin , C. and Kim , D. H. 2008 . Mechanism-based inactivation of cytochrome P450 3A4 by methylenedioxyphenyl lignans from . Acanthopanax chiisanensis. Planta Med. , 74 : 822 – 27 .
   PubMed Web of Science ®Google Scholar
• Yu , L. S. , Wilkinson , C. F. and Anders , M. W. 1980 . Generation of carbon monoxide during the microsomal metabolism of methylenedioxyphenyl compounds . Biochem. Pharmacol. , 29 : 1113 – 22 .
   PubMed Web of Science ®Google Scholar
• Yu , S. J. and Terriere , L. C. 1974 . Bimodal effect of methylenedioxyphenyl compounds on detoxifying enzymes in the housefly . Pest. Biochem. Physiol. , 4 : 160 – 69 .
   Web of Science ®Google Scholar
• Zhu , F. , Parthasarathy , R. , Bai , H. , Woithe , K. , Kaussmann , M. , Nauen , R. , Harrison , D. A. and Palli , S. R. 2010 . A brain-specific cytochrome P450 responsible for the majority of deltamethrin resistance in the QTC279 strain of . Tribolium castaneum. Proc. Natl Acad. Sci. USA , 107 : 8557 – 62 .
   PubMed Web of Science ®Google Scholar