Regulation of dioxin receptor function by different beta-carboline alkaloids

Archives of Toxicology

Volumn 84, Issue 8, 2010, Pages 619-629

  Haarmann Stemmann, Thomas ^a   Sendker, Jandirk ^a   Götz, Christine ^a   Krug, Nathalie ^a   Bothe, Hanno ^a   Fritsche, Ellen ^a,b   Proksch, Peter ^a   Abel, Josef ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

^b UNIVERSITY HOSPITAL RWTH AACHEN   (Germany)

Author keywords

Arylhydrocarbon receptor; Benzo(a)pyrene; Beta carboline alkaloids; Cytochrome P450

Indexed keywords

ALKALOID DERIVATIVE; ANNOMONTINE; AROMATIC HYDROCARBON RECEPTOR; BENZO[A]PYRENE; BETA CARBOLINE; CYTOCHROME P450; RUTAECARPINE; UNCLASSIFIED DRUG; XESTOMANZAMINE A;

ARTICLE; CHEMICAL ANALYSIS; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG MECHANISM; DRUG STRUCTURE; ENZYME ACTIVITY; GENE ACTIVITY; GENE EXPRESSION REGULATION; GENE TARGETING; HEPATOMA CELL; HUMAN; HUMAN CELL; KERATINOCYTE; PRIORITY JOURNAL; PROTEIN FUNCTION;

ALKALOIDS; CARBOLINES; CYTOCHROME P-450 CYP1A1; GENE EXPRESSION; GENE EXPRESSION REGULATION; HEP G2 CELLS; HUMANS; INDOLE ALKALOIDS; PYRIMIDINES; QUINAZOLINES; RECEPTORS, ARYL HYDROCARBON;

EID: 77956230710     PISSN: 03405761     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00204-010-0548-2     Document Type: Article

References (54)

1. P Agostinis M Garmyn A Van Laethem 2007 The Aryl hydrocarbon receptor: an illuminating effector of the UVB response Sci STKE 2007 e49 10.1126/stke.4032007pe49
2. Y Amakura T Tsutsumi K Sasaki M Nakamura T Yoshida T Maitani 2008 Influence of food polyphenols on aryl hydrocarbon receptor-signaling pathway estimated by in vitro bioassay Phytochemistry 69 3117 3130 10.1016/j.phytochem. 2007.07.022 1:CAS:528:DC%2BD1cXhsVCmsL3E 17869316
3. K Asres A Seyoum C Veeresham F Bucar S Gibbons 2005 Naturally derived anti-HIV agents Phytother Res 19 557 581 10.1002/ptr.1629 1:CAS:528: DC%2BD2MXhtFGitLvF 16161055
4. KW Bock C Köhle 2006 Ah receptor: dioxin-mediated toxic responses as hints to deregulated physiologic functions Biochem Pharmacol 72 393 404 10.1016/j.bcp.2006.01.017 1:CAS:528:DC%2BD28XntFWktbY%3D 16545780
5. U Breyer-Pfaff G Wiatr I Stevens HJ Gaertner G Mundle K Mann 1996 Elevated norharman plasma levels in alcoholic patients and controls resulting from tobacco smoking Life Sci 58 1425 1432 10.1016/0024-3205(96)00112-9 1:CAS:528:DyaK28XitFertrw%3D 8622568
6. R Cao W Peng Z Wang A Xu 2007 Beta-carboline alkaloids: biochemical and pharmacological functions Curr Med Chem 14 479 500 10.2174/092986707779940998 1:CAS:528:DC%2BD2sXhs1yhu78%3D 17305548
7. HR Chao YF Wang HT Chen YC Ko EE Chang YJ Huang FY Tsai CH Tsai CH Wu TC Tsou 2007 Differential effect of arecoline on the endogenous dioxin-responsive cytochrome P450 1A1 and on a stably transfected dioxin-responsive element-driven reporter in human hepatoma cells J Hazard Mater 149 234 237 10.1016/j.jhazmat.2007.07.022 1:CAS:528:DC%2BD2sXhtVSksbjK 17707585
8. EV Costa ML Pinheiro CM Xavier JR Silva AC Amaral AD Souza A Barison FR Campos AG Ferreira GM Machado LL Leon 2006 A pyrimidine-beta-carboline and other alkaloids from Annona foetida with antileishmanial activity J Nat Prod 69 292 294 10.1021/np050422s 1:CAS:528:DC%2BD28Xht1equr0%3D 16499336
9. C de Meester 1995 Genotoxic potential of beta-carbolines: a review Mutat Res 339 139 153 1:CAS:528:DyaK2MXpsV2rs74%3D 7491124
10. C Delescluse N Ledirac G de Sousa M Pralavorio D Botta-Fridlund Y Letreut R Rahmani 1997 Comparative study of CYPlAl induction by 3-methylcholanthrene in various human hepatic and epidermal cell types Toxicol In Vitro 11 443 450 10.1016/S0887-2333(97)00077-5 1:CAS:528:DyaK2sXnvFertrw%3D
11. R Dorow R Horowski G Paschelke M Amin 1983 Severe anxiety induced by FG 7142, a beta-carboline ligand for benzodiazepine receptors Lancet 2 98 99 10.1016/S0140-6736(83)90076-4 1:CAS:528:DyaL3sXltlemsr4%3D 6134976
12. D Fekkes A Tuiten I Bom L Pepplinkhuizen 2001 Pharmacokinetics of the beta-carboline norharman in man Life Sci 69 2113 2121 10.1016/S0024-3205(01) 01293-0 1:CAS:528:DC%2BD3MXnt1CrsL0%3D 11669455
13. PM Fernandez-Salguero DM Hilbert S Rudikoff JM Ward FJ Gonzalez 1996 Aryl-hydrocarbon receptor-deficient mice are resistant to 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin-induced toxicity Toxicol Appl Pharmacol 140 173 179 10.1006/taap.1996.0210 1:CAS:528:DyaK28Xls1WisL4%3D 8806883
14. E Fritsche JE Cline NH Nguyen TS Scanlan J Abel 2005 Polychlorinated biphenyls disturb differentiation of normal human neural progenitor cells: clue for involvement of thyroid hormone receptors Environ Health Perspect 113 871 876 10.1289/ehp.7793 1:CAS:528:DC%2BD2MXntVylsb4%3D 16002375
15. E Fritsche C Schafer C Calles T Bernsmann T Bernshausen M Wurm U Hubenthal JE Cline H Hajimiragha P Schroeder LO Klotz A Rannug P Furst H Hanenberg J Abel J Krutmann 2007 Lightening up the UV response by identification of the arylhydrocarbon receptor as a cytoplasmatic target for ultraviolet B radiation Proc Natl Acad Sci USA 104 8851 8856 10.1073/pnas.0701764104 1:CAS:528:DC%2BD2sXmt1aku78%3D 17502624
16. K Gradin A Wilhelmsson L Poellinger A Berghard 1993 Nonresponsiveness of normal human fibroblasts to dioxin correlates with the presence of a constitutive xenobiotic response element-binding factor J Biol Chem 268 4061 4068 1:CAS:528:DyaK3sXisV2ns78%3D 8382688
17. T Haarmann-Stemmann J Abel 2006 The arylhydrocarbon receptor repressor (AhRR): structure, expression, and function Biol Chem 387 1195 1199 10.1515/BC.2006.147 1:CAS:528:DC%2BD28XhtVOhsbfP 16972786
18. T Haarmann-Stemmann H Bothe A Kohli U Sydlik J Abel E Fritsche 2007 Analysis of the transcriptional regulation and molecular function of the aryl hydrocarbon receptor repressor in human cell lines Drug Metab Dispos 35 2262 2269 10.1124/dmd.107.016253 1:CAS:528:DC%2BD2sXhsVeiur3J 17890447
19. T Haarmann-Stemmann H Bothe J Abel 2009 Growth factors, cytokines and their receptors as downstream targets of arylhydrocarbon receptor (AhR) signaling pathways Biochem Pharmacol 77 508 520 10.1016/j.bcp.2008.09.013 1:CAS:528:DC%2BD1MXhs1ahsL0%3D 18848820
20. ME Hahn 2002 Aryl hydrocarbon receptors: diversity and evolution Chem Biol Interact 141 131 160 10.1016/S0009-2797(02)00070-4 1:CAS:528: DC%2BD38Xms12hs70%3D 12213389
21. T Herraiz 2000 Analysis of the bioactive alkaloids tetrahydro-beta- carboline and beta-carboline in food J Chromatogr A 881 483 499 10.1016/S0021-9673(99)01313-8 1:CAS:528:DC%2BD3cXjslOmsbg%3D 10905730
22. T Herraiz H Guillen VJ Aran 2008 Oxidative metabolism of the bioactive and naturally occurring beta-carboline alkaloids, norharman and harman, by human cytochrome P450 enzymes Chem Res Toxicol 21 2172 2180 10.1021/tx8002565 1:CAS:528:DC%2BD1cXht1CltbnO 19238614
23. C Ioannides DF Lewis 2004 Cytochromes P450 in the bioactivation of chemicals Curr Top Med Chem 4 1767 1788 10.2174/1568026043387188 1:CAS:528:DC%2BD2cXhtVKmsbnO 15579107
24. M Iwanari M Nakajima R Kizu K Hayakawa T Yokoi 2002 Induction of CYP1A1, CYP1A2, and CYP1B1 mRNAs by nitropolycyclic aromatic hydrocarbons in various human tissue-derived cells: chemical-, cytochrome P450 isoform-, and cell-specific differences Arch Toxicol 76 287 298 10.1007/s00204-002-0340-z 1:CAS:528:DC%2BD38Xks1Srt78%3D 12107646
25. SK Lee NH Kim J Lee DH Kim ES Lee HG Choi HW Chang Y Jahng TC Jeong 2004 Induction of cytochrome P450 s by rutaecarpine and metabolism of rutaecarpine by cytochrome P450 s Planta Med 70 753 757 10.1055/s-2004-827207 1:CAS:528:DC%2BD2cXnsVals78%3D 15326550
26. SK Lee SR Bista H Jeong DH Kim MJ Kang Y Jahng TC Jeong 2007 The effects of rutaecarpine on the pharmacokinetics of acetaminophen in rats Arch Pharm Res 30 1629 1634 10.1007/BF02977334 1:CAS:528:DC%2BD1cXjsVahu7w%3D 18254252
27. YF Lu M Santostefano BD Cunningham MD Threadgill S Safe 1995 Identification of 3′-methoxy-4′-nitroflavone as a pure aryl hydrocarbon (Ah) receptor antagonist and evidence for more than one form of the nuclear Ah receptor in MCF-7 human breast cancer cells Arch Biochem Biophys 316 470 477 10.1006/abbi.1995.1062 1:CAS:528:DyaK2MXjsV2htrc%3D 7840652
28. DE Machemer RH Tukey 2005 The role of protein kinase C in regulation of TCDD-mediated CYP1A1 gene expression Toxicol Sci 87 27 37 10.1093/toxsci/kfi220 1:CAS:528:DC%2BD2MXovVOjs7k%3D 15947024
29. S Medjakovic A Jungbauer 2008 Red clover isoflavones biochanin A and formononetin are potent ligands of the human aryl hydrocarbon receptor J Steroid Biochem Mol Biol 108 171 177 10.1016/j.jsbmb.2007.10.001 1:CAS:528: DC%2BD1cXhsFyntrs%3D 18060767
30. F Meggio A Donella Deana M Ruzzene A Brunati L Cesaro B Guerra T Meyer H Mett D Fabbro P Furet G Dobrowolska L Pinna 1995 Different susceptibility of protein kinases to staurosporine inhibition. Kinetic studies and molecular bases for the resistance of protein kinase CK2 Eur J Biochem 234 317 322 10.1111/j.1432-1033.1995.317-c.x 1:CAS:528:DyaK2MXpvVCluro%3D 8529658
31. J Mimura M Ema K Sogawa Y Fujii-Kuriyama 1999 Identification of a novel mechanism of regulation of Ah (dioxin) receptor function Genes Dev 13 20 25 10.1101/gad.13.1.20 1:CAS:528:DyaK1MXnvF2hsA%3D%3D 9887096
32. YJ Moon X Wang ME Morris 2006 Dietary flavonoids: effects on xenobiotic and carcinogen metabolism Toxicol In Vitro 20 187 210 10.1016/j.tiv.2005.06.048 1:CAS:528:DC%2BD28XksVensQ%3D%3D 16289744
33. AJ Murk J Legler MS Denison JP Giesy C van de Guchte A Brouwer 1996 Chemical-activated luciferase gene expression (CALUX): a novel in vitro bioassay for Ah receptor active compounds in sediments and pore water Fundam Appl Toxicol 33 149 160 10.1006/faat.1996.0152 1:CAS:528:DyaK28Xls1CktLc%3D 8812260
34. DW Nebert TP Dalton AB Okey FJ Gonzalez 2004 Role of aryl hydrocarbon receptor-mediated induction of the CYP1 enzymes in environmental toxicity and cancer J Biol Chem 279 23847 23850 10.1074/jbc.R400004200 1:CAS:528: DC%2BD2cXksV2jurY%3D 15028720
35. H Nishihashi Y Kanno K Tomuro T Nakahama Y Inouye 2006 Primary structure and organ-specific expression of the rat aryl hydrocarbon receptor repressor gene Biol Pharm Bull 29 640 647 10.1248/bpb.29.640 1:CAS:528: DC%2BD28XkslOis70%3D 16595894
36. CM Palermo CA Westlake TA Gasiewicz 2005 Epigallocatechin gallate inhibits aryl hydrocarbon receptor gene transcription through an indirect mechanism involving binding to a 90 kDa heat shock protein Biochemistry 44 5041 5052 10.1021/bi047433p 1:CAS:528:DC%2BD2MXitVynsbo%3D 15794642
37. S Park EC Henry TA Gasiewicz 2000 Regulation of DNA binding activity of the ligand-activated aryl hydrocarbon receptor by tyrosine phosphorylation Arch Biochem Biophys 381 302 312 10.1006/abbi.2000.1999 1:CAS:528: DC%2BD3cXmsFemsLc%3D 11032419
38. W Pfau K Skog 2004 Exposure to beta-carbolines norharman and harman J Chromatogr B Analyt Technol Biomed Life Sci 802 115 126 10.1016/j.jchromb.2003. 10.044 1:CAS:528:DC%2BD2cXht1yjsLg%3D 15036003
39. P Ramadoss C Marcus GH Perdew 2005 Role of the aryl hydrocarbon receptor in drug metabolism Expert Opin Drug Metab Toxicol 1 9 21 10.1517/17425255.1.1.9 1:CAS:528:DC%2BD2MXmvVGhsrc%3D 16922649
40. AC Rovescalli N Brunello C Franzetti G Racagni 1986 Interaction of putative endogenous tryptolines with the hypothalamic serotonergic system and prolactin secretion in adult male rats Neuroendocrinology 43 603 610 10.1159/000124588 1:CAS:528:DyaL28XkslehtL8%3D 2427964
41. JV Schmidt GH Su JK Reddy MC Simon CA Bradfield 1996 Characterization of a murine Ahr null allele: involvement of the Ah receptor in hepatic growth and development Proc Natl Acad Sci U S A 93 6731 6736 10.1073/pnas.93.13.6731 1:CAS:528:DyaK28XjvFeisbg%3D 8692887
42. SD Seidel V Li GM Winter WJ Rogers EI Martinez MS Denison 2000 Ah receptor-based chemical screening bioassays: application and limitations for the detection of Ah receptor agonists Toxicol Sci 55 107 115 10.1093/toxsci/55.1. 107 1:CAS:528:DC%2BD3cXjtVeht7o%3D 10788565
43. J Sheu 1999 Pharmacological effects of rutaecarpine, an alkaloid isolated from Evodia rutaecarpa Cardiovasc Drug Rev 17 237 245 1:CAS:528: DC%2BD3cXos1Gnuw%3D%3D
44. Y Totsuka T Takamura-Enya R Nishigaki T Sugimura K Wakabayashi 2004 Mutagens formed from beta-carbolines with aromatic amines J Chromatogr B Analyt Technol Biomed Life Sci 802 135 141 10.1016/j.jchromb.2003.10.041 1:CAS:528:DC%2BD2cXht1yjsLY%3D 15036005
45. Y Tsuchiya M Nakajima S Itoh M Iwanari T Yokoi 2003 Expression of aryl hydrocarbon receptor repressor in normal human tissues and inducibility by polycyclic aromatic hydrocarbons in human tumor-derived cell lines Toxicol Sci 72 253 259 10.1093/toxsci/kfg022 1:CAS:528:DC%2BD3sXisFCjsrc%3D 12655030
46. YF Ueng JJ Wang LC Lin SS Park CF Chen 2001 Induction of cytochrome P450-dependent monooxygenase in mouse liver and kidney by rutaecarpine, an alkaloid of the herbal drug Evodia rutaecarpa Life Sci 70 207 217 10.1016/S0024-3205(01)01390-X 1:CAS:528:DC%2BD3MXpt1ShsL0%3D 11787945
47. YF Ueng WC Jan LC Lin TL Chen FP Guengerich CF Chen 2002 The alkaloid rutaecarpine is a selective inhibitor of cytochrome P450 1A in mouse and human liver microsomes Drug Metab Dispos 30 349 353 10.1124/dmd.30.3.349 1:CAS:528:DC%2BD38Xhtl2qtL0%3D 11854157
48. YF Ueng TH Tsai MJ Don RM Chen TL Chen 2005 Alteration of the pharmacokinetics of theophylline by rutaecarpine, an alkaloid of the medicinal herb Evodia rutaecarpa, in rats J Pharm Pharmacol 57 227 232 10.1211/0022357055489 1:CAS:528:DC%2BD2MXht1els70%3D 15720787
49. JP Vanden Heuvel GC Clark CL Thompson Z McCoy CR Miller GW Lucier DA Bell 1993 CYP1A1 mRNA levels as a human exposure biomarker: use of quantitative polymerase chain reaction to measure CYP1A1 expression in human peripheral blood lymphocytes Carcinogenesis 14 2003 2006 10.1093/carcin/14.10.2003
50. P Venault G Chapouthier 2007 From the behavioral pharmacology of beta-carbolines to seizures, anxiety, and memory ScientificWorldJournal 7 204 223 10.1100/tsw.2007.48 1:CAS:528:DC%2BD2sXit1ajsb0%3D 17334612
51. CF Vogel F Matsumura 2009 A new cross-talk between the aryl hydrocarbon receptor and RelB, a member of the NF-kappaB family Biochem Pharmacol 77 734 745 10.1016/j.bcp.2008.09.036 1:CAS:528:DC%2BD1MXhs1ahtr0%3D 18955032
52. AM Yu JR Idle KW Krausz A Kupfer FJ Gonzalez 2003 Contribution of individual cytochrome P450 isozymes to the O-demethylation of the psychotropic beta-carboline alkaloids harmaline and harmine J Pharmacol Exp Ther 305 315 322 10.1124/jpet.102.047050 1:CAS:528:DC%2BD3sXis1amsr4%3D 12649384
53. X Zeng X Zeng 1999 Relationship between the clinical effects of berberine on severe congestive heart failure and its concentration in plasma studied by HPLC Biomed Chromatogr 13 442 444 10.1002/(SICI)1099-0801(199911)13:7<442:: AID-BMC908>3.0.CO;2-A 1:CAS:528:DyaK1MXnsFSis7Y%3D 10534753
54. S Zhang C Qin SH Safe 2003 Flavonoids as aryl hydrocarbon receptor agonists/antagonists: effects of structure and cell context Environ Health Perspect 111 1877 1882 1:CAS:528:DC%2BD2cXit1OqtA%3D%3D 14644660