Xanthohumol influences preadipocyte differentiation: Implication of antiproliferative and apoptotic effects

Journal of Agricultural and Food Chemistry

Volumn 56, Issue 24, 2008, Pages 11631-11637

  Mendes, Vanda ^a,b   Monteiro, Rosário ^a,b   Pestana, Diogo ^a   Teixeira, Diana ^a,b   Calhau, Conceição ^a   Azevedo, Isabel ^a  

^a University of Porto   (Portugal)

^b UNIVERSITY OF PORTO   (Portugal)

Author keywords

Adipocyte; Adipogenesis; Apoptosis; NF B; Obesity; Proliferation; Xanthohumol

Indexed keywords

HUMULUS LUPULUS;

GROWTH INHIBITOR; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; PLANT EXTRACT; PROPIOPHENONE DERIVATIVE; XANTHOHUMOL;

ADIPOCYTE; ANIMAL; APOPTOSIS; ARTICLE; CELL DIFFERENTIATION; CELL PROLIFERATION; CELL STRAIN 3T3; CHEMISTRY; DRUG EFFECT; HUMULUS; METABOLISM; MOUSE; PHYSIOLOGY;

ADIPOCYTES; ANIMALS; APOPTOSIS; CELL DIFFERENTIATION; CELL PROLIFERATION; GROWTH INHIBITORS; HUMULUS; MICE; NF-KAPPA B; NIH 3T3 CELLS; PLANT EXTRACTS; PROPIOPHENONES;

EID: 58849106396     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf802233q     Document Type: Article

References (39)

1. Abelson, P.; Kennedy, D. The obesity epidemic. Science 2004, 304 (5676), 1413.
2. Frühbeck, G.; Gómez-Ambrosi, J.; Muruzábal, F. J.; Burrell, M. A. The adipocyte: a model for integration of endocrine and metabolic signaling in energy metabolism regulation. Am. J. Physiol. Endocrinol. Metab. 2001, 280 (6), E827-47.
3. Lafontan, M. Fat cells: afferent and efferent messages define new approaches to treat obesity. Annu. Rev. Pharmacol. Toxicol. 2005, 45, 119-46.
4. Cancello, R.; Clement, K. Is obesity an inflammatory illness? Role of low-grade inflammation and macrophage infiltration in human white adipose tissue. Bjog 2006, 113 (10), 1141-7.
5. Xu, H.; Barnes, G. T.; Yang, Q.; Tan, G.; Yang, D.; Chou, C. J.; Sole, J.; Nichols, A.; Ross, J. S.; Tartaglia, L. A.; Chen, H. Chronic inflammation in fat plays a crucial role in the development of obesity-related insulin resistance. J. Clin. Invest. 2003, 112 (12), 1821-30.
6. Bays, H. E.; Gonzalez-Campoy, J. M.; Bray, G. A.; Kitabchi, A. E.; Bergman, D. A.; Schorr, A. B.; Rodbard, H. W.; Henry, R. R. Pathogenic potential of adipose tissue and metabolic consequences of adipocyte hypertrophy and increased visceral adiposity. Expert Rev. Cardiovasc. Ther. 2008, 6 (3), 343-68.
7. Avram, M. M.; Avram, A. S.; James, W. D. Subcutaneous fat in normal and diseased states 3. Adipogenesis: from stem cell to fat cell. J. Am. Acad. Dermatol. 2007, 56 (3), 472-92.
8. Miller, W. H., Jr.; Faust, I. M.; Hirsch, J. Demonstration of de novo production of adipocytes in adult rats by biochemical and radioautographic techniques. J. Lipid Res. 1984, 25 (4), 336-47.
9. Monteiro, R.; de Castro, P. M.; Calhau, C.; Azevedo, I. Adipocyte size and liability to cell death. Obes. Surg. 2006, 16 (6), 804-6.
10. Sethi, J. K.; Vidal-Puig, A. J. Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J. Lipid Res. 2007, 48 (6), 1253-62.
11. Cooke, P. S.; Naaz, A. Effects of estrogens and the phytoestrogen genistein on adipogenesis and lipogenesis in males and females. Birth Defects Res. A Clin. Mol. Teratol. 2005, 73 (7), 472-3.
12. Lin, J.; Della-Fera, M. A.; Baile, C. A. Green tea polyphenol epigallocatechin gallate inhibits adipogenesis and induces apoptosis in 3T3-L1 adipocytes. Obes. Res. 2005, 13 (6), 982-90.
13. Pinent, M.; Blade, C.; Salvadó, M. J.; Blay, M.; Pujadas, G.; Fernández-Larrea, J.; Arola, L.; Ardévol, A. Procyanidin effects on adipocyte-related pathologies. Crit. Rev. Food Sci. Nutr. 2006, 46 (7), 543-50.
14. Rayalam, S.; Della-Fera, M. A.; Baile, C. A. Phytochemicals and regulation of the adipocyte life cycle. J. Nutr. Biochem. 2008, doi: 10.1016/j.jnutbio.2007.12.007.
15. Stevens, J. F.; Page, J. E. Xanthohumol and related prenylflavonoids from hops and beer: to your good health! Phytochemistry 2004, 65 (10), 1317-30.
16. Miranda, C. L.; Yang, Y. H.; Henderson, M. C.; Stevens, J. F.; Santana-Rios, G.; Deinzer, M. L.; Buhler, D. R. Prenylflavonoids from hops inhibit the metabolic activation of the carcinogenic heterocyclic amine 2-amino-3-methylimidazo[4, 5-f]quinoline, mediated by cDNA-expressed human CYP1A2. Drug Metab. Dispos. 2000, 28 (11), 1297-302.
17. 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), 1296-305.
18. 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), 235-51.
19. Gerhauser, C.; Alt, A.; Heiss, E.; GamalEldeen, 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), 959-69.
20. Zhao, F.; Nozawa, H.; Daikonnya, A.; Kondo, K.; Kitanaka, S. Inhibitors of nitric oxide production from hops (Humulus lupulus L.). Biol. Pharm. Bull. 2003, 26 (1), 61-5.
21. Goto, K.; Asai, T.; Hara, S.; Namatame, I.; Tomoda, H.; Ikemoto, M.; Oku, N. Enhanced antitumor activity of xanthohumol, a diacylglycerol acyltransferase inhibitor, under hypoxia. Cancer Lett. 2005, 219 (2), 215-22.
22. Albini, A.; Dell'Eva, R.; Vene, R.; Ferrari, N.; Buhler, D. R.; Noonan, D. M.; Fassina, G. Mechanisms of the antiangiogenic activity by the hop flavonoid xanthohumol: NF-kappaB and Akt as targets. FASEB J 2006, 20 (3), 527-9.
23. 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.
24. Monteiro, R.; Faria, A.; Azevedo, I.; Calhau, C. Modulation of breast cancer cell survival by aromatase inhibiting hop (Humulus lupulus L.) flavonoids. J. Steroid Biochem. Mol. Biol. 2007, 105 (1-5), 124-30.
25. 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-A(y) mice. Biochem. Biophys. Res. Commun. 2005, 336 (3), 754-61.
26. Yang, J. Y.; Della-Fera, M. A.; Rayalam, S.; Baile, C. A. Effect of xanthohumol and isoxanthohumol on 3T3-L1 cell apoptosis and adipogenesis. Apoptosis 2007, 12 (11), 1953-63.
27. Yang, J. Y.; Della-Fera, M. A.; Rayalam, S.; Baile, C. A. Enhanced effects of xanthohumol plus honokiol on apoptosis in 3T3-L1 adipocytes. Obesity (Silver Spring) 2008.
28. Magalhaes, P. J.; Guido, L. F.; Cruz, J. M.; Barros, A. A. Analysis of xanthohumol and isoxanthohumol in different hop products by liquid chromatography-diode array detection-electrospray ionization tandem mass spectrometry. J. Chromatogr. A 2007, 1150 (1-2), 295-301.
29. Miranda, C. L.; Stevens, J. F.; Helmrich, A.; Henderson, M. C.; Rodriguez, R. J.; Yang, Y. H.; Deinzer, M. L.; Barnes, D. W.; Buhler, D. R. Antiproliferative and cytotoxic effects of prenylated flavonoids from hops (Humulus lupulus) in human cancer cell lines. Food Chem. Toxicol. 1999, 37 (4), 271-85.
30. Rosen, E. D.; Spiegelman, B. M. Molecular regulation of adipogenesis. Annu. Rev. Cell Dev. Biol. 2000, 16, 145-71.
31. Rosen, E. D.; Sarraf, P.; Troy, A. E.; Bradwin, G.; Moore, K.; Milstone, D. S.; Spiegelman, B. M.; Mortensen, R. M. PPAR gamma is required for the differentiation of adipose tissue in vivo and in vitro. Mol. Cell 1999, 4 (4), 611-7.
32. Pan, L.; Becker, H.; Gerhauser, C. Xanthohumol induces apoptosis in cultured 40-16 human colon cancer cells by activation of the death receptor- and mitochondrial pathway. Mol. Nutr. Food Res. 2005, 49 (9), 837-43.
33. Gilmore, T. D. Introduction to NF-kappaB: players, pathways, perspectives. Oncogene 2006, 25 (51), 6680-4.
34. Chae, G. N.; Kwak, S. J. NF-kappaB is involved in the TNF-alpha induced inhibition of the differentiation of 3T3-L1 cells by reducing PPARgamma expression. Exp. Mol. Med. 2003, 35 (5), 431-7.
35. Nikolic, D.; Li, Y.; Chadwick, L. R.; Pauli, G. F.; van Breemen, R. B. Metabolism of xanthohumol and isoxanthohumol, prenylated flavonoids from hops (Humulus lupulus L.), by human liver microsomes. J. Mass. Spectrom. 2005, 40 (3), 289-99.
36. Nookandeh, A.; Frank, N.; Steiner, F.; Ellinger, R.; Schneider, B.; Gerhauser, C.; Becker, H. Xanthohumol metabolites in faeces of rats. Phytochemistry 2004, 65 (5), 561-70.
37. Yilmazer, M.; Stevens, J. F.; Buhler, D. R. In vitro glucuronidation of xanthohumol, a flavonoid in hop and beer, by rat and human liver microsomes. FEBS Lett. 2001, 491 (3), 252-6.
38. Yilmazer, M.; Stevens, J. F.; Deinzer, M. L.; Buhler, D. R. In vitro biotransformation of xanthohumol, a flavonoid from hops (Humulus lupulus), by rat liver microsomes. Drug Metab. Dispos. 2001, 29 (3), 223-31.
39. Cinti, S.; Mitchell, G.; Barbatelli, G.; Murano, I.; Ceresi, E.; Faloia, E.; Wang, S.; Fortier, M.; Greenberg, A. S.; Obin, M. S. Adipocyte death defines macrophage localization and function in adipose tissue of obese mice and humans. J. Lipid Res. 2005, 46 (11), 2347-55.