Xanthohumol uptake and intracellular kinetics in hepatocytes, hepatic stellate cells, and intestinal cells

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 24, 2011, Pages 12893-12901

  Wolff, Horst ^a   Motyl, Magdalena ^b   Hellerbrand, Claus ^c   Heilmann, Jörg ^b   Kraus, Birgit ^b  

^a INSTITUTE OF EPIDEMIOLOGY   (Germany)

^b UNIVERSITY OF REGENSBURG   (Germany)

^c UNIVERSITY HOSPITAL REGENSBURG   (Germany)

Author keywords

FRAP; hepatic stellate cells; intracellular concentration; liver cells; xanthohumol

Indexed keywords

FRAP; HEPATIC STELLATE CELLS; INTRACELLULAR CONCENTRATION; LIVER CELLS; XANTHOHUMOL;

BIOCHEMISTRY; CELL CULTURE; CELLS; FLUORESCENCE; PHOTOBLEACHING; VISUALIZATION;

MOLECULAR BIOLOGY;

FLAVONOID; PROPIOPHENONE DERIVATIVE; XANTHOHUMOL;

ARTICLE; BIOAVAILABILITY; CELL CULTURE; CELL STRAIN CACO 2; CHEMISTRY; HUMAN; HUMULUS; INTESTINE; KINETICS; LIVER CELL; LIVER CELL CARCINOMA; LIVER TUMOR; METABOLISM; STELLATE CELL; TUMOR CELL LINE;

BIOLOGICAL AVAILABILITY; CACO-2 CELLS; CARCINOMA, HEPATOCELLULAR; CELL LINE, TUMOR; CELLS, CULTURED; FLAVONOIDS; HEPATIC STELLATE CELLS; HEPATOCYTES; HUMANS; HUMULUS; INTESTINES; KINETICS; LIVER NEOPLASMS; PROPIOPHENONES;

EID: 84255176255     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf203689z     Document Type: Article

References (39)

1. Gerhauser, C.; Alt, A.; Heiss, E.; Gamal-Eldeen, A.; Klimo, K.; Knauft, J.; Neumann, I.; Scherf, H. R.; Frank, N.; Bartsch, H.; Becker, H. Cancer chemopreventive activity of xanthohumol, a natural product derived from hop Mol. Cancer Ther. 2002, 1 (11) 959-969
2. Stevens, J. F.; Page, J. E. Xanthohumol and related prenylflavonoids from hops and beer: to your good health! Phytochemistry 2004, 65 (10) 1317-1330
3. Ferk, F.; Huber, W. W.; Filipic, M.; Bichler, J.; Haslinger, E.; Misik, M.; Nersesyan, A.; Grasl-Kraupp, B.; Zegura, B.; Knasmuller, S. Xanthohumol, a prenylated flavonoid contained in beer, prevents the induction of preneoplastic lesions and DNA damage in liver and colon induced by the heterocyclic aromatic amine amino-3-methyl-imidazo[4,5- f ]quinoline (IQ) Mutat. Res. 2010, 691 (1-2) 17-22
4. Drenzek, J. G.; Seiler, N. L.; Jaskula-Sztul, R.; Rausch, M. M.; Rose, S. L. Xanthohumol decreases Notch1 expression and cell growth by cell cycle arrest and induction of apoptosis in epithelial ovarian cancer cell lines Gynecol. Oncol. 2011, 122 (2) 396-401
5. Negrao, R.; Costa, R.; Duarte, D.; Taveira Gomes, T.; Mendanha, M.; Moura, L.; Vasques, L.; Azevedo, I.; Soares, R. Angiogenesis and inflammation signaling are targets of beer polyphenols on vascular cells J. Cell Biochem. 2010, 111 (5) 1270-1279
6. Gerhauser, C.; Frank, N. Xanthohumol, a new all-rounder? Mol. Nutr. Food Res. 2005, 49 (9) 821-823
7. Wang, Q.; Ding, Z. H.; Liu, J. K.; Zheng, Y. T. Xanthohumol, a novel anti-HIV-1 agent purified from hops Humulus lupulus Antiviral Res. 2004, 64 (3) 189-194
8. Monteiro, R.; Calhau, C.; Silva, A. O.; Pinheiro-Silva, S.; Guerreiro, S.; Gartner, F.; Azevedo, I.; Soares, R. Xanthohumol inhibits inflammatory factor production and angiogenesis in breast cancer xenografts J. Cell Biochem. 2008, 104 (5) 1699-1707
9. Harikumar, K. B.; Kunnumakkara, A. B.; Ahn, K. S.; Anand, P.; Krishnan, S.; Guha, S.; Aggarwal, B. B. Modification of the cysteine residues in IκBα kinase and NF-κB (p65) by xanthohumol leads to suppression of NF-κB-regulated gene products and potentiation of apoptosis in leukemia cells Blood 2009, 113 (9) 2003-2013
10. Lupinacci, E.; Meijerink, J.; Vincken, J. P.; Gabriele, B.; Gruppen, H.; Witkamp, R. F. Xanthohumol from hop (Humulus lupulus L.) is an efficient inhibitor of monocyte chemoattractant protein-1 and tumor necrosis factor-α release in LPS-stimulated RAW 264.7 mouse macrophages and U937 human monocytes J. Agric. Food Chem. 2009, 57 (16) 7274-7281
11. Lee, I. S.; Lim, J.; Gal, J.; Kang, J. C.; Kim, H. J.; Kang, B. Y.; Choi, H. J. Anti-inflammatory activity of xanthohumol involves heme oxygenase-1 induction via NRF2-ARE signaling in microglial BV2 cells Neurochem. Int. 2011, 58 (2) 153-160
12. Meissner, O.; Haberlein, H. Influence of xanthohumol on the binding behavior of GABAA receptors and their lateral mobility at hippocampal neurons Planta Med. 2006, 72 (7) 656-658
13. Pang, Y.; Nikolic, D.; Zhu, D.; Chadwick, L. R.; Pauli, G. F.; Farnsworth, N. R.; van Breemen, R. B. Binding of the hop (Humulus lupulus L.) chalcone xanthohumol to cytosolic proteins in Caco-2 intestinal epithelial cells Mol. Nutr. Food Res. 2007, 51 (7) 872-879
14. Bracke, M. E.; Vanhoecke, B. W.; Derycke, L.; Bolca, S.; Possemiers, S.; Heyerick, A.; Stevens, C. V.; De Keukeleire, D.; Depypere, H. T.; Verstraete, W.; Williams, C. A.; McKenna, S. T.; Tomar, S.; Sharma, D.; Prasad, A. K.; DePass, A. L.; Parmar, V. S. Plant polyphenolics as anti-invasive cancer agents Anticancer Agents Med. Chem. 2008, 8 (2) 171-185
15. Hanske, L.; Loh, G.; Sczesny, S.; Blaut, M.; Braune, A. Recovery and metabolism of xanthohumol in germ-free and human microbiota-associated rats Mol. Nutr. Food Res. 2010, 54 (10) 1405-1413
16. Dietz, B. M.; Kang, Y. H.; Liu, G.; Eggler, A. L.; Yao, P.; Chadwick, L. R.; Pauli, G. F.; Farnsworth, N. R.; Mesecar, A. D.; van Breemen, R. B.; Bolton, J. L. Xanthohumol isolated from Humulus lupulus inhibits menadione-induced DNA damage through induction of quinone reductase Chem. Res. Toxicol. 2005, 18 (8) 1296-1305
17. Henderson, M. C.; Miranda, C. L.; Stevens, J. F.; Deinzer, M. L.; Buhler, D. R. In vitro inhibition of human P450 enzymes by prenylated flavonoids from hops, Humulus lupulus Xenobiotica 2000, 30 (3) 235-251
18. Liu, G.; Eggler, A. L.; Dietz, B. M.; Mesecar, A. D.; Bolton, J. L.; Pezzuto, J. M.; van Breemen, R. B. Screening method for the discovery of potential cancer chemoprevention agents based on mass spectrometric detection of alkylated Keap1 Anal. Chem. 2005, 77 (19) 6407-6414
19. Dorn, C.; Kraus, B.; Motyl, M.; Weiss, T. S.; Gehrig, M.; Scholmerich, J.; Heilmann, J.; Hellerbrand, C. Xanthohumol, a chalcon derived from hops, inhibits hepatic inflammation and fibrosis Mol. Nutr. Food Res. 2010, 54 (Suppl. 2) S205-S213
20. Dorn, C.; Weiss, T. S.; Heilmann, J.; Hellerbrand, C. Xanthohumol, a prenylated chalcone derived from hops, inhibits proliferation, migration and interleukin-8 expression of hepatocellular carcinoma cells Int. J. Oncol. 2010, 36 (2) 435-441
21. Plazar, J.; Filipic, M.; Groothuis, G. M. Antigenotoxic effect of xanthohumol in rat liver slices Toxicol In Vitro 2008, 22 (2) 318-327
22. Plazar, J.; Zegura, B.; Lah, T. T.; Filipic, M. Protective effects of xanthohumol against the genotoxicity of benzo(a)pyrene (BaP), 2-amino-3-methylimidazo[4,5- f ]quinoline (IQ) and tert -butyl hydroperoxide (t-BOOH) in HepG2 human hepatoma cells Mutat. Res. 2007, 632 (1-2) 1-8
23. Nakabayashi, H.; Taketa, K.; Miyano, K.; Yamane, T.; Sato, J. Growth of human hepatoma cells lines with differentiated functions in chemically defined medium Cancer Res. 1982, 42 (9) 3858-3563
24. Zweibaum, A.; Triadou, N.; Kedinger, M.; Augeron, C.; Robine-Leon, S.; Pinto, M.; Rousset, M.; Haffen, K. Sucrase-isomaltase: a marker of foetal and malignant epithelial cells of the human colon Int. J. Cancer 1983, 32 (4) 407-412
25. Schnabl, B.; Choi, Y. H.; Olsen, J. C.; Hagedorn, C. H.; Brenner, D. A. Immortal activated human hepatic stellate cells generated by ectopic telomerase expression Lab Invest. 2002, 82 (3) 323-33
26. Schaefer, L. H.; Schuster, D.; Herz, H. Generalized approach for accelerated maximum likelihood based image restoration applied to three-dimensional fluorescence microscopy J. Microsc. 2001, 204 (Part 2) 99-107
27. Braeckmans, K.; Peeters, L.; Sanders, N. N.; De Smedt, S. C.; Demeester, J. Three-dimensional fluorescence recovery after photobleaching with the confocal scanning laser microscope Biophys. J. 2003, 85 (4) 2240-2252
28. Reits, E. A.; Neefjes, J. J. From fixed to FRAP: measuring protein mobility and activity in living cells Nat. Cell Biol. 2001, 3 (6) E145-E147
29. Hauser, G. I.; Seiffert, S.; Oppermann, W. Systematic evaluation of FRAP experiments performed in a confocal laser scanning microscope - part II: Mmultiple diffusion processes J. Microsc. 2008, 230 (Part 3) 353-362
30. Seiffert, S.; Oppermann, W. Systematic evaluation of FRAP experiments performed in a confocal laser scanning microscope J. Microsc. 2005, 220 (Part 1) 20-30
31. Imamura, H.; Kawasaki, S.; Shiga, J.; Bandai, Y.; Sanjo, K.; Idezuki, Y. Quantitative evaluation of parenchymal liver cell volume and total hepatocyte number in cirrhotic patients Hepatology 1991, 14 (3) 448-453
32. Axelrod, D.; Koppel, D. E.; Schlessinger, J.; Elson, E.; Webb, W. W. Mobility measurement by analysis of fluorescence photobleaching recovery kinetics Biophys. J. 1976, 16 (9) 1055-1069
33. Lee, S. H.; Kim, H. J.; Lee, J. S.; Lee, I. S.; Kang, B. Y. Inhibition of topoisomerase I activity and efflux drug transporters' expression by xanthohumol. from hops Arch. Pharm. Res. 2007, 30 (11) 1435-1439
34. Taur, J. S.; Rodriguez-Proteau, R. Effects of dietary flavonoids on the transport of cimetidine via P-glycoprotein and cationic transporters in Caco-2 and LLC-PK1 cell models Xenobiotica 2008, 38 (12) 1536-1550
35. Pohjala, L.; Tammela, P.; Samanta, S. K.; Yli-Kauhaluoma, J.; Vuorela, P. Assessing the data quality in predictive toxicology using a panel of cell lines and cytotoxicity assays Anal. Biochem. 2007, 362 (2) 221-228
36. Vogel, S.; Ohmayer, S.; Brunner, G.; Heilmann, J. Natural and non-natural prenylated chalcones: synthesis, cytotoxicity and anti-oxidative activity Bioorg. Med. Chem. 2008, 16 (8) 4286-4293
37. Wang, W. S.; Ye, Y. H.; Zhou, Y. W. New prenylchalcones from the hops of Humulus lupulus J. Asian Nat. Prod. Res. 2008, 10 (5-6) 485-490
38. Araujo, J. R.; Goncalves, P.; Martel, F. Chemopreventive effect of dietary polyphenols in colorectal cancer cell lines. Nutr. Res. (N.Y.) 31 (2), 77-87.
39. Schempp, H.; Vogel, S.; Huckelhoven, R.; Heilmann, J. Re-evaluation of superoxide scavenging capacity of xanthohumol Free Radical Res. 2010, 44 (12) 1435-1444