Inhibition of TNFα-induced activation of nuclear factor κB by kava (Piper methysticum) derivatives

Biochemical Pharmacology

Volumn 71, Issue 8, 2006, Pages 1206-1218

  Folmer, Florence ^a   Blasius, Romain ^b   Morceau, Franck ^b   Tabudravu, Jioji ^a   Dicato, Mario ^b   Jaspars, Marcel ^a   Diederich, Marc ^b  

^a UNIVERSITY OF ABERDEEN   (United Kingdom)

^b LABORATOIRE DE BIOLOGIE MOLÉCULAIRE ET CELLULAIRE DU CANCER   (Luxembourg)

Author keywords

Chalcones; Ethnopharmacology; K562; Kava; Lactones; NF B; TNF

Indexed keywords

DIHYDROKAWAIN; FLAVOKAVAIN A; FLAVOKAVAIN B; I KAPPA B; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; KAVA EXTRACT; KAWAIN; MITOGEN ACTIVATED PROTEIN KINASE 3; MITOGEN ACTIVATED PROTEIN KINASE P38; PROTEIN P50; SYNAPTOTAGMIN; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG; I KAPPA B KINASE; KAVA; LUCIFERASE; PLANT MEDICINAL PRODUCT; TRANSCRIPTION FACTOR RELA;

ARTICLE; ASTHMA; CELL VIABILITY; CONTROLLED STUDY; CYTOPLASM; DNA RESPONSIVE ELEMENT; DRUG EFFECT; DRUG MECHANISM; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; GENE EXPRESSION; GENE TRANSLOCATION; GENETIC TRANSCRIPTION; HUMAN; HUMAN CELL; PIPER METHYSTICUM; PRIORITY JOURNAL; PROTEIN DEGRADATION; PROTEIN PHOSPHORYLATION; TRADITIONAL MEDICINE; URINARY TRACT INFECTION; WESTERN BLOTTING; CELL NUCLEUS; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; GEL MOBILITY SHIFT ASSAY; GENETIC TRANSFECTION; GENETICS; ISOLATION AND PURIFICATION; METABOLISM; PLANT ROOT; PROTEIN TRANSPORT; REPORTER GENE; TUMOR CELL LINE;

BLOTTING, WESTERN; CELL LINE, TUMOR; CELL NUCLEUS; CELL SURVIVAL; CYTOPLASM; DOSE-RESPONSE RELATIONSHIP, DRUG; ELECTROPHORETIC MOBILITY SHIFT ASSAY; GENE EXPRESSION; GENES, REPORTER; HUMANS; I-KAPPA B KINASE; KAVA; LUCIFERASES; MOLECULAR STRUCTURE; NF-KAPPA B; NF-KAPPA B P50 SUBUNIT; PLANT PREPARATIONS; PLANT ROOTS; PROTEIN TRANSPORT; TRANSCRIPTION FACTOR RELA; TRANSFECTION; TUMOR NECROSIS FACTOR-ALPHA;

EID: 33644821070     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2005.12.032     Document Type: Article

References (37)

1. A.J. Garcia-Pineres, M.T. Lindenmeyer, and I. Merfort Role of cysteine residues of p65/NF-kappa B on the inhibition by the sesquiterpene lactone parthenolide and-N-ethyl maleimide, and on its transactivating potential Life Sci 75 7 2004 841 856
2. M.W. Mayo, and A.S. Baldwin The transcription factor NF-kappa B: control of oncogenesis and cancer therapy resistance Biochim Biophys Acta Rev Cancer 1470 2 2000 M55 M62
3. S. Shishodia, and B.B. Aggarwal Nuclear factor κB: a friend or a foe in cancer? Biochem Pharmacol 68 6 2004 1071 1080
4. B.B. Aggarwal, Y. Takada, S. Shishodia, A.M. Gutierrez, O.V. Oommen, and H. Ichikawa Nuclear transcription factor NF-kappa B: role in biology and medicine Indian J Exp Biol 42 2 2004 341 353
5. M. Karin, Y. Yamamoto, and Q.M. Wang The IKKNF-kappa B system: a treasure trove for drug development Nat Rev Drug Discov 3 1 2004 17 26
6. A. Garg, and B.B. Aggarwal Nuclear transcription factor-kappa B as a target for cancer drug development Leukaemia 16 6 2002 1053 1068
7. Z.W. Sun, and R. Andersson NF-kappa b activation and inhibition: a review Shock 18 2 2002 99 106
8. V. Pande, R.K. Sharma, J.I. Inoue, M. Otsuka, and M.J. Ramos A molecular modeling study of inhibitors of nuclear factor κB (p50)-DNA binding J Comput Aid Mol Des 17 12 2003 825 836
9. B. Haefner NF-kappa B: arresting a major culprit in cancer Drug Discov Today 7 12 2002 653 663
10. S. Muller, R. Murillo, V. Castro, V. Brecht, and I. Merfort Sesquiterpene lactones from Montanoa hibiscifolia that inhibit the transcription factor NF-kappa B J Nat Prod 67 4 2004 622 630
11. P. Bremner, and M. Heinrich Natural products as targeted modulators of the nuclear factor κB pathway J Pharm Pharmacol 54 4 2002 453 472
12. C.H. Hocart, B. Fankhauser, and D.W. Buckle Chemical archaeology of kava, a potent brew Rapid Commun Mass Spectrom 7 3 1993 219 224
13. P.M. Dewick Medicinal natural products: a biosynthetic approach 2002 John Wiley and Sons Ltd. Chichester
14. A.R. Bilia, L. Scalise, M.C. Bergonzi, and F.F. Vincieri Analysis of kavalactones from Piper methysticum (kava-kava) J Chromatogr B: Anal Technol Biomed Life Sci 812 1-2 2004 203 214
15. D. Wu, M.G. Nair, and D.L. DeWitt Novel compounds from Piper methysticum Forst (Kava kava) roots and their effect on cyclooxygenase enzyme J Agric Food Chem 50 4 2002 701 705
16. D. Wu, L. Yu, M.G. Nair, D.L. DeWitt, and R.S. Ramsewak Cyclooxygenase enzyme inhibitory compounds with antioxidant activities from Piper methysticum (kava kava) roots Phytomedicine 9 1 2002 41 47
17. Y.N. Singh Kava-an overview J Ethnopharmacol 37 1 1992 13 45
18. P.V. Nerurkar, K. Dragull, and C.S. Tang In vitro toxicity of kava alkaloid, pipermethystine, in HepG2 cells compared to kavalactones Toxicol Sci 79 1 2004 106 111
19. K. Dragull, W.Y. Yoshida, and C.S. Tang Piperidine alkaloids from Piper methysticum Phytochemistry 63 2 2003 193 198
20. S.M. Kupchan, R.W. Britton, M.F. Ziegle, and C.W. Sigel Bruceantin, a new potent antileukemic simaroubolide from Brucea antidysenterica J Org Chem 38 1 1973 178 179
21. Y. Shao, K. He, B.L. Zheng, and Q.Y. Zheng Reversed-phase high-performance liquid chromatographic method for quantitative analysis of the six major kavalactones in Piper methysticum J Chromatogr A 825 1 1998 1 8
22. H.R.W. Dharmaratne, N.P.D. Nanayakkara, and I.A. Khan Kavalactones from Piper methysticum, and their C-13 NMR spectroscopic analyses Phytochemistry 59 4 2002 429 433
23. A. Duvoix, S. Delhalle, R. Blasius, M. Schnekenburger, F. Morceau, and M. Fougere Effect of chemopreventive agents on glutathione S-transferase P1-1 gene expression mechanisms via activating protein 1 and nuclear factor κB inhibition Biochem Pharmacol 68 6 2004 1101 1111
24. J. Bain, H. McLauchlan, M. Elliott, and P. Cohen The specificities of protein kinase inhibitors: an update Biochem J 371 2003 199 204
25. E.G.W. Schijlen, C.H.R. de Vos, A.J. van Tunen, and A.G. Bovy Modification of flavonoid biosynthesis in crop plants Phytochemistry 65 19 2004 2631 2648
26. H.H. Ko, L.T. Tsao, K.L. Yu, C.T. Liu, J.P. Wang, and C.N. Lin Structure-activity relationship studies on chalcone derivatives: the potent inhibition of chemical mediators release Bioorg Med Chem 11 1 2003 105 111
27. S. Iwata, T. Nishino, N. Nagata, Y. Satomi, H. Nishino, and S. Shibata Antitumorigenic activities of chalcones.1 Inhibitory effects of chalcone derivatives on (32)Pi-incorporation into phospholipids of HeLa cells promoted by 12-O-tetradecanoyl-phorbol 13-acetate (TPA) Biol Pharm Bull 18 12 1995 1710 1713
28. S. Iwata, T. Nishino, H. Inoue, N. Nagata, Y. Satomi, and H. Nishino Antitumorigenic activities of chalcones-(II) photo-isomerization of chalcones and the correlation with their biological activities Biol Pharm Bull 20 12 1997 1266 1270
29. B. Madan, S. Batra, and B. Ghosh 2'-Hydroxychalcone inhibits nuclear factor κB and blocks tumor necrosis factor-alpha-and lipopolysaccharide- induced adhesion of neutrophils to human umbilical vein endothelial cells Mol Pharmacol 58 3 2000 526 534
30. X. Zi, and A.R. Simoneau Flavokavain A, a novel chalcone from kava extract, induces apoptosis in bladder cancer cells by involvement of Bax protein-dependent and mitochondria-dependent apoptotic pathway and suppresses tumor growth in mice Cancer Res 65 8 2005 3479 3486
31. T. Hashimoto, M. Suganuma, H. Fujiki, M. Yamada, T. Kohno, and Y. Asakawa Isolation and synthesis of TNF-alpha release inhibitors from Fijian kawa (Piper methysticum) Phytomedicine 10 4 2003 309 317
32. G.J. Kapadia, M.A. Azuine, H. Tokuda, E. Hang, T. Mukainaka, and H. Nishino Inhibitory effect of herbal remedies on 12-O-tetradecanoylphorbol-13- acetate-promoted Epstein-Barr virus early antigen activation Pharmacol Res 45 3 2002 213 220
33. J.E. Jung, T.K. Kim, J.S. Lee, S.Y. Oh, S. Kwak, and X. Jin Survivin inhibits anti-growth effect of p53 activated by aurora B Biochem Biophys Res Commun 336 4 2005 1164 1171
34. D. Zhang, K. Li, C.L. Erickson-Miller, M. Weiss, and D.M. Wojchowski DYRK gene structure and erythroid-restricted features of DYRK3 gene expression Genomics 85 1 2005 117 130
35. P.A. Kelly, and Z. Rahmani DYRK1A enhances the mitogen-activated protein kinase cascade in PC12 cells by forming a complex with Ras, B-Raf, and MEK1 Mol Biol Cell 16 8 2005 3562 3573
36. L. New, Y. Jiang, and J. Han Regulation of PRAK subcellular location by p38 MAP kinases Mol Biol Cell 14 6 2003 2603 2616
37. S. Pugazhenthi, E. Miller, C. Sable, P. Young, K.A. Heidenreich, and L.M. Boxer Insulin-like growth factor-I induces bcl-2 promoter through the transcription factor cAMP-response element-binding protein J Biol Chem 274 39 1999 27529 27535