Cytotoxic and apoptotic effects of the oxidized derivatives of stigmasterol in the u937 human monocytic cell line

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 19, 2010, Pages 10793-10798

  O'Callaghan, Yvonne C ^a   Foley, David A ^b   O'Connell, Niamh M ^b   Mccarthy, Florence O ^b   Maguire, Anita R ^c   O'Brien, Nora M ^a  

^a School of Food and Nutritional Sciences   (Ireland)

^b Analytical and Biological Chemistry Research Facility   (Ireland)

^c UNIVERSITY COLLEGE CORK   (Ireland)

Author keywords

Apoptosis; Cytotoxicity; Stigmasterol oxidation products; U937

Indexed keywords

APOPTOSIS; APOPTOTIC; APOPTOTIC EFFECTS; APOPTOTIC PROTEINS; CYTOTOXIC; CYTOTOXIC EFFECTS; DIETARY EXPOSURE; GLUTATHIONES; IN-CELL; MONOCYTIC CELLS; PHYTOSTEROL OXIDATION PRODUCTS; STIGMASTEROL OXIDATION PRODUCTS; U937; U937 CELL;

ALCOHOLS; CELL CULTURE; CELL DEATH; CHOLESTEROL; OLEFINS; OXIDATION;

CYTOTOXICITY;

ANTIOXIDANT; EPOXIDE; STIGMASTEROL;

APOPTOSIS; ARTICLE; CELL STRAIN U937; CELL SURVIVAL; CHEMISTRY; DNA FRAGMENTATION; DRUG EFFECT; HUMAN; MONOCYTE; OXIDATION REDUCTION REACTION; ULTRASTRUCTURE;

ANTIOXIDANTS; APOPTOSIS; CELL SURVIVAL; DNA FRAGMENTATION; EPOXY COMPOUNDS; HUMANS; MONOCYTES; OXIDATION-REDUCTION; STIGMASTEROL; U937 CELLS;

EID: 78049246727     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf1023017     Document Type: Article

References (30)

1. Ryan, E.; McCarthy, F.; Maguire, A.; O'Brien, N. Phytosterol oxidation products: Their formation, occurance and biological effects. Food Rev. Int. 2009, 25, 157-174.
2. Sottero, B.; Gamba, P.; Gargiulo, S.; Leonarduzzi, G.; Poli, G. Cholesterol oxidation products and disease: An emerging topic of interest in medicinal chemistry. Curr. Med. Chem. 2009, 16, 685-705.
3. Lordan, S.; Mackrill, J. J.; O'Brien, N. M. Oxysterols and mechanisms of apoptotic signaling: Implications in the pathology of degenerative diseases. J. Nutr. Biochem. 2009, 20, 321-336.
4. Meyer, W.; Jungnickel, H.; Janijke, M.; Dettner, K.; Spitellier, G. On the cytotoxicity of oxidised phytosterols isolated from photoautotrophic cell cultures of Chenopodium rubrum tested on meal worms Tenebrio molitor. Phytochemistry 1998, 47, 789-797.
5. Adcox, C.; Boyd, L.; Oehrl, L.; Allen, J.; Fenner, G. Comparative effects of phytosterol oxides and cholesterol oxides in cultured macrophage-derived cell lines. J. Agric. Food Chem. 2001, 49, 2090-2095.
6. Maguire, L.; Konoplyannikov, M.; Ford, A.; Maguire, A. R.; O'Brien, N. M. Comparison of the cytotoxic effects of β-sitosterol oxides and a cholesterol oxide, 7β-hydroxycholesterol, in cultured mammalian cells. Br. J. Nutr. 2003, 90, 767-775.
7. McCarthy, F. O.; Chopra, J.; Ford, A.; Hogan, S. A.; Kerry, J. P.; O'Brien, N. M.; Ryan, E.; Maguire, A. R. Synthesis, isolation and characterisation of β-sitosterol and β-sitosterol oxide derivatives. Org. Biomol. Chem. 2005, 3, 3059-3065.
8. Ryan, E.; Chopra, J.; McCarthy, F; Maguire, A.; O'Brien, N. Qualitative and quantitative comparison of the cytotoxic and apoptotic potential of phytosterol oxidation products with their corresponding cholesterol oxidation products. Br. J. Nutr. 2005, 94, 443-451.
9. Foley, D. A.; O'Callaghan, Y.; O'Brien, N. M.; McCarthy, F. O.; Maguire, A. R. Synthesis and characterisation of stigmasterol oxidation products. J. Agric. Food Chem. 2010, 58, 1165-1173.
10. Grandgirard, A.; Martine, L.; Joffre, C.; Juaneda, P.; Berdeaux, O. Gas chromatographic separation and mass spectrometric identification of mixtures of oxyphytosterol and oxycholesterol derivatives: Application to a phytosterol-enriched food. J. Chromatogr., A 2004, 1040, 239-250.
11. Bortolomeazzi, R.; Cordaro, F.; Pizzale, L.; Conte, L. S. Presence of phytosterol oxides in crude vegetable oils and their fate during refining. J. Agric. Food Chem. 2003, 51, 2394-2401.
12. Grandgirard, A.; Martine, L.; Demaison, L.; Cordelet, C.; Joffre, C.; Berdeaux, O.; Semon, E. Oxyphytosterols are present in plasma of healthy human subjects. Br. J. Nutr. 2004, 91, 101-106.
13. Ryan, L.; O'Callaghan, Y. C.; O'Brien, N. M. Generation of an oxidative stress precedes caspase activation during 7β-hydroxycholesterol- induced apoptosis in U937 cells. J. Biochem. Mol. Toxicol. 2004, 18, 50-59.
14. Phelan, M.; Aherne, S. A.; Wong, A.; O'Brien, N. M. Bioactive properties of wood knot extracts on cultured human cells. J. Med. Food 2009, 6, 1245-1251
15. Smith, P. K.; Krohn, R. I.; Hermanson, G. T.; Mallia, A. K.; Gartner, F. H.; Provenzano, M. D.; Fujimoto, F. K.; Goeke, N. M.; Olsen, B. J.; Klenk, D. C. Measurement of protein using bicinchoninic acid. Anal. Chem. 1985, 150, 76-85.
16. Koschutnig, K.; Heikkinen, S.; Kemmo, S.; Lampi, A. M.; Piironen, V.; Wagner, K. H. Cytotoxic and apoptotic effects of single and mixed oxides of β-sitosterol on HepG2 cells. Toxicol. in Vitro 2009, 23, 755-762.
17. O'Callaghan, Y. C.; Woods, J. A.; O'Brien, N. M. Characteristics of 7β-hydroxycholesterol-induced cell death in a human monocytic blood cell line, U937 and a human hepatoma cell line, HepG2. Toxicol. in Vitro 2002, 16, 245-251.
18. Lizard, G.; Monier, S.; Cordelet, C.; Gesquière, L.; Deckert, V.; Gueldry, S.; Lagrost, L.; Gambert, P. Characterization and comparison of the mode of cell death, apoptosis versus necrosis, induced by 7β- hydroxycholesterol and 7-ketocholesterol in the cells of the vascular wall. Arterioscler. Thromb. Vasc. Biol. 1999, 19, 1190-1200.
19. O'Sullivan, A. J.; O'Callaghan, Y. C.; O'Brien, N. M. Differential effects of mixtures of cholesterol oxidation products on bovine aortic endothelial cells and human monocytic U937 cells. Int. J. Toxicol. 2005, 24, 173-179.
20. Leonarduzzi, G.; Sottero, B.; Poli, G. Oxidised products of cholesterol: Dietary and metabolic origin, and proatherosclerotic effects (review). J. Nutr. Biochem. 2002, 13, 700-710.
21. Massey, J. B.; Pownall, H. J. Structures of biologically active oxysterols determine their differential effects on phospholipid membranes. Biochemistry 2006, 45, 10747-10758.
22. Leonarduzzi, G.; Vizio, B.; Sottero, B.; Verde, V.; Gamba, P.; Mascia, C.; Chiarpotto, E.; Poli, G.; Biasi, F. Early involvement of ROS overproduction in apoptosis induced by 7-ketocholesterol. Antioxid. Redox Signal. 2006, 8, 375-380.
23. Lyons, N. M.; Woods, J. A.; O'Brien, N. M. R-Tocopherol, but not γ-tocopherol, inhibits 7β-hydroxycholesterol-induced apoptosis in human U937 cells. Free Radical Res. 2001, 35, 329-339.
24. Vejux, A.; Guyot, S.; Montange, T.; Riedinger, J. M.; Kahn, E.; Lizard, G. Phospholipidosis and down-regulation of the PI3-K/PDK-1/Akt signalling pathway are vitamin E inhibitable events associated with 7-ketocholesterol- induced apoptosis. J. Nutr. Biochem. 2009, 1, 45-61.
25. Palozza, P.; Simone, R.; Catalano, A.; Boninsegna, A.; Bohm, V.; Frohlich, K.; Mele, M. C.; Monego, G.; Ranelletti, F. O. Lycopene prevents 7-ketocholesterol-induced oxidative stress, cell cycle arrest and apoptosis in human macrophages. J. Nutr. Biochem. 2010, 34, 34-46.
26. Ryan, L.; O'Callaghan, Y. C.; O'Brien, N. M. Oxidised products of cholesterol: Their role in apoptosis. Curr. Nutr. Food Sci. 2005, 1, 41-51.
27. Ryan, L.; O'Callaghan, Y. C.; O'Brien, N. M. Comparison of the apoptotic processes induced by the oxysterols 7β-hydroxycholesterol and cholesterol-5β,6β-epoxide. Cell Biol. Toxicol. 2004, 5, 313-323.
28. Lizard, G.; Gueldry, S.; Sordet, O.; Monier, S.; Athias, A.; Miguet, C.; Bessede, G.; Lemarie, S.; Solary, E.; Gambert, P. Glutathione is implied in the control of 7-ketocholesterol-induced apoptosis, which is associated with radical oxygen species production. FASEB J. 1998, 12, 1651-1663.
29. Fadeel, B.; Hassan, Z.; Hellström-Lindberg, E.; Henter, J. I.; Orrenius, S.; Zhivotovsky, B. Cleavage of Bcl-2 is an early event in chemotherapy-induced apoptosis of human myeloid leukemia cells. Leukemia 1999, 13, 719-728.
30. Ryan, L.; O'Callaghan, Y. C.; O'Brien, N. M. The role of the mitochondria in apoptosis induced by 7β-hydroxycholesterol and cholesterol-5β, 6β-epoxide. Br. J. Nutr. 2005, 94, 519-525.