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

Journal of Agricultural and Food Chemistry

Volumn 57, Issue 16, 2009, Pages 7274-7281

  Lupinacci, Elvira ^a   Meijerink, Jocelijn ^a   Vincken, Jean Paul ^a   Gabriele, Bartolo ^b   Gruppen, Harry ^a   Witkamp, Renger F ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

^b UNIVERSITY OF CALABRIA   (Italy)

Author keywords

(TNF ); Hop; Humulus lupulus; Macrophages; Monocyte chemoattractant protein 1 (MCP 1); Obesity; RAW 264.7; Tumor necrosis factor ; U937

Indexed keywords

FLAVONOID; LIPOPOLYSACCHARIDE; MONOCYTE CHEMOTACTIC PROTEIN 1; PROPIOPHENONE DERIVATIVE; TUMOR NECROSIS FACTOR ALPHA; XANTHOHUMOL;

ANIMAL; ARTICLE; CELL LINE; CHEMISTRY; DOWN REGULATION; DRUG EFFECT; HUMAN; HUMULUS; IMMUNOLOGY; MACROPHAGE; MONOCYTE; MOUSE;

ANIMALS; CELL LINE; CHEMOKINE CCL2; DOWN-REGULATION; FLAVONOIDS; HUMANS; HUMULUS; LIPOPOLYSACCHARIDES; MACROPHAGES; MICE; MONOCYTES; PROPIOPHENONES; TUMOR NECROSIS FACTOR-ALPHA;

HUMULUS; HUMULUS LUPULUS;

EID: 70349197988     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf901244k     Document Type: Article

References (36)

1. Bray, G. A. Medical consequences of obesity. J. Clin. Endocrinol. Metab. 2004, 89, 2583-2589.
2. Kershaw, E. E.; Flier, J. S. Adipose tissue as an endocrine organ. J. Clin. Endocrinol. Metab. 2004, 59, 2548-2556.
3. Guilherme, A.; Virbesius, J. V.; Puri, V.; Czech, M. P. Adipocytes dysfunctions linking obesity to insuline resistance and type 2 diabetes. Nat. Rev. Mol. Cell. Biol. 2008, 9, 367-377.
4. Hotamisligil, G. S. Inflammation and metabolic disorders. Nature 2006, 444, 860-867.
5. Sartipy, P.; Loskutoff, D. J. Monocyte chemoattractant protein 1 in obesity and insulin resistance. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 7265-7270. (Pubitemid 36706427)
6. Baggiolini, M. Chemokines and leukocyte traffic. Nature 1998, 392, 565-568.
7. Christiansen, T.; Richelsen, B.; Bruun, J. M. Monocyte chemoat-tractant protein-1 is produced in isolated adipocytes, associated with adiposity and reduced after weight loss in morbid obese subjects. Int. J. Obes. Relat. Metab. Disord. 2005, 29, 146-150.
8. Weisberg, S. P.; McCann, D.; Desai, M.; Rosenbaum, M.; Leibel, R. L.; Ferrante, A. W. Obesity is associated with macrophage accumulation in adipose tissue. J. Clin. Invest. 2003, 112, 1796-1808. (Pubitemid 38063703)
9. Yu, R.; Kim, C. S.; Kwon, B. S.; Kawada, T. Mesenteric adipose tissue derived monocyte chemoattractant protein-1 plays a crucial role in adipose tissue macrophage migration and activation in obese mice. Obesity 2006, 14, 1353-1362. (Pubitemid 46219660)
10. Simpson, W. J.; Smith, A. R. W. Factors affecting antibacterial activity of hop compounds and their derivatives. J. Appl. Bacteriol. 1992, 72, 327-334.
11. Zanoli, P.; Zavatti, M. Pharmacognostic and pharmacological profile of Humulus lupulus L. J. Ethnopharmacol 2008, 116, 383-396.
12. Cho, Y.-C.; Kim, H. J.; Kim, Y.-J.; Lee, K. Y.; Choi, H. J.; Lee, I.-S.; Kang, B. Y. Differential anti-inflammatory pathway by xanthohumol in IFN-γ and LPS-activated macrophages. Int. Immunopharmacol. 2008, 8, 567-573.
13. Zhao, F.; Nozawa, H.; Daikonnya, A.; Kondo, K.; Kitanaka, S. Inhibition of nitric oxide production from hops (Humulus lupulus L). Biol. Pharm. Bull. 2003, 26, 61-65.
14. 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, 959-969.
15. Tobe, H.; Muraki, Y.; Kitamura, K.; Komiyama, O.; Sato, Y.; Sugioka, T.; Maruyama, H. B.; Matsuda, E.; Nagai, M. Bone resorption inhibitors from hop extract. Biosci., Biotechnol., Biochem. 1997, 61, 158-159. (Pubitemid 27164864)
16. Lee, J. C.; Kundu, J. K.; Hwang, D.-M.; Na, H.-K.; Surh, Y.-J. Humulone inhibits phorbol ester-induced COX-2 expression in mouse skin by blocking activation of NF-κB and AP-1: IκB kinase and c-Jun-N-terminal kinase as respective potential upstream targets. Carcinogenesis 2007, 28, 1491-1498.
17. Yajima, H.; Ikeshima, E.; Shiraki, M.; Kanaya, T.; Fujiwara, D.; Odai, H.; Tsuboyama-Kasaoka, N.; Ezaki, O.; Oikawa, S.; Kondo, K. Isohumulones, bitter acids derived from hops, activate both peroxisome proliferator-activated receptor α and γ and reduce insulin resistance. J. Biol. Chem. 2004, 279, 33456-33462.
18. Garcia-Villalba, R.; Cortacero-Ramirez, S.; Segura-Carretero, A.; Martin-Lagos Contreras, J. S.; Fernandez-Gutierrez, A. Analysis of hop acids and their oxidized derivatives and iso-a-acids in beer by capillary electrophoresis-electrospray ionization mass spectrometry. J. Agric. Food Chem. 2006, 54, 5400-5409. (Pubitemid 44195719)
19. Vanhoenacker, G.; De Keukeleire, D.; Sandra, P. Analysis of iso-α-acids and reduced iso-α-acids in beer by direct injection and liquid chromatography with ultraviolet absorbance detection or with mass spectrometry. J. Chromatogr., A 2004, 1035, 53-61. (Pubitemid 38446796)
20. Helmja, K.; Vaher, M.; Pussa, T.; Kamsol, K.; Orav, A.; Kaljurand, M. Bioactive components of the hop strobilus: comparison of different extraction methods by capillary electrophoretic and chromatographic methods. J. Chromatogr., A 2001, 1155, 222-229.
21. Stevens, J. F.; Ivancic, M.; Hsu, V. L.; Deinzer, M. L. Prenylflavonoids from Humulus lupulus. Phytochemistry 1997, 44, 1575-1585.
22. Hofte, A. J. P.; van der Hoeven, R. A. M. Characterization of hop acids by liquid chromatography with negative electrospray ionization mass spectrometry. J. Am. Soc. Brew. Chem. 1998, 56, 118-122. (Pubitemid 29032303)
23. Cawthorn, W. P.; Sethi, J. K. TNF-α and adipocyte biology. FEBS Lett. 2008, 552, 117-131.
24. Dahlman, I.; Kaaman, M.; Olsson, T.; Tan, G. D.; Bickerton, A. S. T.; Wahlen, K.; Andersson, J.; Arvidsson Nordstrom, E.; Blomqvist, L.; Sjogren, A.; Forsgren, M.; Attersand, A.; Amer, P. A unique role of MCP-1 among chemokines in adipose tissue of obese subjects. J. Clin. Endocrinol Metab. 2005, 90, 5834-5840.
25. Kanda, H.; Tateya, S.; Tamori, Y.; Kotani, K.; Hiasa, K.; Kitazawa, R.; Kitazawa, S.; Miyachi, H.; Maeda, S.; Egashira, K.; Kasuga, M. MCP-1 contributes to macrophage infiltration into adipose tissue, insulin resistance, and hepatic steatosis in obesity. J. Clin. Invest. 2006, 116, 1494-1505. (Pubitemid 43911004)
26. Stevens, J. F.; Page, J. E. Xanthohumol and related prenylflavonoids from hops and beer: to your good health!. Phytochemistry 2004, 65, 1317-1330.
27. Monteiro, R.; Calhau, C.; Oliveira e Silva, A.; 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, 1699-1707.
28. Lust, S.; Vanhoecke, B.; Janssens, A.; Philippe, J.; Bracke, M.; Offner, F. Xanthohumol kills B-chronic lymphocytic leukemia cells by an apoptotic mechanism. Mol. Nutr. Food Res. 2005, 49, 844-850. (Pubitemid 41411568)
29. Colgate, E. C.; Miranda, C. L.; Stevens, J. F.; Bray, T. M.; Ho, E. Xanthohumol, a prenylflavonoid derived from hops induces apoptosis and inhibits NF-κβ activation in prostate epithelial cells. Cancer Lett. 2001, 246, 201-209.
30. Casaschi, A.; Maiyoh, G. K.; Rubio, B. K.; Li, R. W.; Adeli, K.; Theriault, A. G. The chalcone xanthohumol inhibits triglyceride and apolipoprotein B secretion in HepG2 cells. J. Nutr. 2004, 134, 1340-1346.
31. Nozawa, H. Xanthohumol, the chalcone from beer hops (Humulus lupulus L.), is the ligand for farnesoid X receptor and ameliorates lipid and glucose metabolism in KK-Ay mice. Biochem. Biophys. Res. Commun. 2005, 336, 754-761.
32. Simeoni, E.; Hoffmann, M. M.; Winkelmann, B. R.; Ruiz, J.; Fleury, S.; Boehm, B. O.; Marz, W.; Vassalli, G. Association between the A-2518G polymorphism in the monocyte chemoattractant protein-1 gene and insulin resistance and type 2 diabetes mellitus. Diabetologia 2004, 47, 1574-1580. (Pubitemid 39371640)
33. 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-KB -regulated gene products and potentiation of apoptosis in leukemia cells. Blood 2009, 113, 2003-2013.
34. Yajima, H.; Noguchi, T.; Ikeshima, E.; Shiraki, M.; Kanaya, T.; Tsuboyama-Kasaoka, N.; Ezaki, O.; Oikawa, S.; Kondo, K. Prevention of diet-induced obesity by dietary isomerized hop extract containing isohumulones in rodents. Int. J. Obes. 2005, 29, 991-997. (Pubitemid 41076240)
35. Toyoda, T.; Kamei, Y.; Kato, H.; Sugita, S.; Takeya, M.; Suganami, T.; Ogawa, Y. Effect of peroxisome proliferator-activated receptor-α ligands in the interaction between adipocytes and macrophages in obese adipose tissue. Obesity 2008, 16, 1199-1207. (Pubitemid 351771340)
36. 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. 2001, 51, 872-879.