Phytosterol oxidation products: Their formation, occurrence, and biological effects

Food Reviews International

Volumn 25, Issue 2, 2009, Pages 157-174

  Ryan, Eileen ^a   McCarthy, Florence O ^a   Maguire, Anita R ^a   O'Brien, Nora M ^a  

^a UNIVERSITY COLLEGE CORK   (Ireland)

Author keywords

Absorption; Cytotoxicity; Food content; Oxides; Phytosterol

Indexed keywords

BIOLOGICAL EFFECTS; FUNCTIONAL FOODS; NATURAL COMPONENTS; PHYTOSTEROL; PHYTOSTEROL OXIDATION PRODUCTS; PLANT STEROLS;

ABSORPTION; ALCOHOLS; CELL MEMBRANES; CYTOTOXICITY; OXIDATION; OXIDES; SEED;

OILS AND FATS;

EID: 61949141501     PISSN: 87559129     EISSN: 15256103     Source Type: Journal    
DOI: 10.1080/87559120802682797     Document Type: Article

References (81)

1. Ostlund, R.E., Jr. Phytosterols in human nutrition. J. Nutr. Biochem. 2002, 22, 533-549.
2. Ostlund, R.E., Jr. Phytosterols, cholesterol absorption and healthy diets. Lipids 2007, 42, 41-45.
3. Kuhlmann, K.; Lindtner, O.; Bauch, A.; Ritter, G.; Woerner, B.; Niemann, B. Simulation of prospective phytosterol intake in Germany by novel functional, foods. Brit. J. Nutr. 2005, 93, 377-385.
4. Tai, C.Y.; Chen, Y.C.; Chen, B.H. Analysis, formation and inhibition of cholesterol oxidation products in foods: an overview (part I). J. Food Drag Anal. 1999, 7, 243-257.
5. Daly, G.G.; Finocchiaro, E.T.; Richardson, T. Characterization of some oxidation products of β-sitosterol. J. Agric. Food Chem. 1983, 31, 46-50.
6. Lampi, A.M.; Juntunen, L.; Toivo, J.; Piironen, V. Determination of thermo-oxidation products of plant sterols. J. Chromatogr. B 2002, 777, 83-92.
7. Gordon, M.H.; Magos, P. Products from the autooxidation of Δ-5-avenasterol. Food Chem. 1984, 14, 295-301.
8. th International Rapeseed Congress, Canberra, Australia. 1999, This article is available from: http://www.regional.org.au/au/gci.rc/1/349.htm
9. Saynajoki, S.; Sundberg, S.; Soupas, L.; Lampi, A.M.; Piironen, V. Determination of stigmasterol primary oxidation products by high performance liquid chromatography. Food Chem. 2003, 80, 415-421.
10. Zhang, X.; Julien-David, D.; Miesch, M.; Raul, F.; Geoffroy, P.; Aoude-Werner, D.; Ennahar, S.; Marchioni, E. Quantitative analysis of β-sitosterol oxides induced in vegetable oils by natural sunlight; artificially generated light; and irradiation. J. Agric. Food Chem. 2006, 54, 5410-5415.
11. Grandgirard, A.; Martine, L.; Joffre, C.; Juaneda, P.; Berdeaux, O. Gas chromatographic separation and mass spectrometric identification of mixtures of oxyphytosterols and oxycholesterol derivatives. Application to a phytosterol-enriched food. J. Chromatogr. A 2004, 1040, 239-250.
12. D'Evoli, L.D.; Huikko, L.; Lampi, A.M.; Lucarini, M.; Lombardi-Boccia, G.; Nicoli, S.; Piironen, V. Influence of rosemary (Rosmarinus officinalis. L.) on plant sterol oxidation in extra virgin olive oil. Mol Nutr Food Res 2006, 50, 818-823.
13. Lee, K.; Herian, A.M.; Higley, N.A. Sterol oxidation products in French fries and potato chips. J. Food Prot. 1985, 48, 158-161.
14. Johnsson, L.; Dutta, P.C. Determination of phytosterol oxides in some food products by using an optimized transesterification method. Food Chem. 2005, 1064, 213-217.
15. Giuffrida, F.; Destaillats, F.; Robert, F.; Skibsted, L.H.; Dionisi, F. Formation and hydrolysis of triacylglycerol and sterol epoxides: role of unsaturated triacylglycerol peroxyl radicals. Free Radic. Biol. Med. 2004, 37, 104-114.
16. Aringer, L.; Nordstrom, L. Chromatographic properties and mass spectrometric fragmentation of deoxygenated C27-, C28-, C29-steroids. Biomed. Mass Spectrom. 1981, 8, 183-203.
17. Dutta, P.C. Studies on phytosterol oxides. II: Content in some vegetable oils and in French fries prepared in these oils. J. Am. Oil Chem. Soc. 1997, 74, 659-666.
18. Dutta, P.C.; Appelqvist, L.A. Sterols and sterol oxides in the potato products, and sterols in the vegetable oils used for industrial frying operations. Grasas Aceites 1996, 47, 38-47.
19. Dutta, P.C.; Appelqvist, L.A. Studies on phytosterol oxides. 1: Effect of storage on the content in potato chips in different vegetable oils. J. Am. Oil Chem. Soc. 1997, 74, 647-657.
20. 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.
21. Zhang, X.; Julien-David, D.; Miesch, M.; Geoffroy, P.; Raul, F.; Roussi, S.; Aoudé-Werner, D.; Marchioni, E. Identification and quantitative analysis of β-sitosterol oxides in vegetable oils by capillary gas chromatography-mass spectrometry. Steroids 2005, 70, 896-906.
22. Soupas, L.; Huikko, L.; Lampi, A.M.; Piironen, V. Pan-frying may induce phytosterol oxidation. Food Chem. 2007, 101, 286-297.
23. Rudzinska, M.; Uchman, W.; Wagsowicz, E. Plant sterols in food technology. Acta Sci. Pol. Technol. Ailment. 2005, 4, 147-156.
24. Conchillo, A.; Cercaci, L.; Ansorena, D.; Rodriguez-Estrada, M.T.; Lercker, G.; Astiasarán, I. Levels of phytosterol oxides in enriched and non-enriched spreads: Application of a thin-layer chromatography-gas chromatography methodology. J. Agric. Food Chem. 2005, 53, 7884-7850.
25. Nourooz-Zadeh, J.; Appelqvist, L.A. Isolation and quantitative determination of sterol oxides in plant-based foods: soybean oil and wheat flour. J. Am. Oil Chem. Soc. 1992, 69, 288-293.
26. Cercaci, L.; Conchillo, A.; Rodriguez-Estrada, M.T.; Ansorena, D.; Astiasaran, I.; Lercker, G. Preliminary study on health-related lipid components of bakery products. J. Food Protect. 2006, 69, 1393-1401.
27. Zunin, P.; Calcagno, C.; Evangelisti, F. Sterol oxidation in infant milk formulas and milk cereals. J. Dairy Res. 1998, 65, 591-598.
28. Garcia-Llatas, G.; Cercaci, L.; Rodriguez-Estrada, M.T.; Lagarda, M.J.; Fabre, R.; Lercker, G. Sterol oxidation in ready-to-eat infant foods during storage. J. Agric. Food Chem. In Press.
29. Turchetto, E.; Lercker, G.; Bortolomeazzi, R. Oxisterol determination in selected coffees. Toxicol. Ind. Health 1993, 9, 519-527.
30. Soupas, L.; Juntunen, L.; Lampi, A.M.; Piironen, V. Effects of sterol structure, temperature, and lipid medium on phytosterol oxidation. J. Agric. Food Chem. 2004, 54, 6485-6491.
31. Soupas, L.; Huikko, L.; Lampi, A.M.; Piironen, V. Esterification affects phytosterol oxidation. Eur. J. Lipid Sci. Technol. 2005, 107, 107-118.
32. Yanishlieva, N.; Schiller, H.; Marinova, E. Autooxidation of sitosterol. II: Main products formed at ambient temperature and high temperature treatment with oxygen. Riv. Ital. Sostanze Grasse 1980, 57, 572-576.
33. Cercaci, L.; Rodriguez-Estrada, M.T.; Lercker, G.; Decker, E.A. Phytosterol oxidation in oil-in-water emulsions and bulk oil. Food Chem. 2007, 102, 161-167.
34. Lambelet, P.; Grandgirard A.; Gregoire, S.; Juaneda, P.; Sebedio, J.L.; Bertoli, C Formation of modified fatty acids and oxyphytosterols during refining of low eracic rapeseed oil. J. Agric. Food Chem. 2003, 51, 4284-4290.
35. Niewiadomski, H. The sterol hydrocarbons in edible oils. Nahrung 1975, 19, 525-536.
36. Rudzinska, M.; Korczak, J.; Gramza, A.; Wagsowicz, E. Inhibition of stigmasterol oxidation products by antioxidants in purified sunflower oil. J. A.O.A.C Int. 2004, 87, 499-504.
37. Guardiola, F.; Bou, R.; Boatella, J.; Codony, R. Analysis of sterol oxidation products in foods. J. A.O.A.C. Int. 2004, 87, 441-465.
38. 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.
39. Aringer, L.; Eneroth, P. Formation and metabolism in vitro of 5, 6-epoxides of cholesterol and β-sitosterol. J. Lipid Res. 1974, 15, 389-398.
40. Aringer, L.; Eneroth, P. Studies on the formation of C7-oxygenated cholesterol and β-sitosterol metabolites in cell-free preparations of rat liver. J. Lipid Res. 1973, 14, 563-572.
41. Aringer, L.; Eneroth, P.; Nordstrom, L. Side chain hydroxylation of cholesterol, campesterol, and ß-sitosterol in rat liver mitochondria. J Lipid Res. 1976, 17, 263-272
42. Ostlund, R.E. Jr.; McGill, J.B.; Zeng, C.M.; Covey, D.F.; Stearns, J.; Stenson, W.F.; Spilburg, C.A. Gastrointestinal absorption and plasma kinetics of soy Delta (5)-phytosterols and phytostanols in humans. Am. J. Physiol. Endocrinol. Metab. 2002, 282, E911-E916.
43. Bosner, M.S.; Lange, L.G.; Stenson, W.F.; Ostlund, R.E. Jr. Percent cholesterol absorption in normal women and men quantified with dual stable isotopic tracers and negative ion mass spectrometry. J. Lipid Res. 1999, 40, 302-308.
44. Wang, D.Q.H. Regulation of Intestinal cholesterol absorption. Annual Rev. Physiol. 2007, 69, 221-248.
45. Tomoyori, H.; Kawata, Y.; Higuchi, T.; Ichi, I.; Sato, H.; Sato, M.; Ikeda, I.; Imaizumi, K. Phytosterol oxidation products are absorbed in the intestinal lymphatics in rats but do not accelerate atherosclerosis in apolipoprotein-E deficient mice. J. Nutr. 2004, 134, 1690-1696.
46. Grandgirard, A.; Sergiel, J.P.; Nour, M.; Demaison-Meloche, J.; Ginies, C. Lymphatic absorption of phytosterol oxides in rats. Lipids 1999, 34, 563-570.
47. Gylling, H.; Miettinen, T.A. Plant sterols in nutrition. Scand. J. Nutr. 2000, 44, 155-157.
48. Sudhop, T.; von Bergmann, K. Sitosterolemia: a rare disease. Z. Kardiol. 2004, 93, 921-928.
49. Plat, J.; Bragt, M.C.E.; Mensink, R.P. Common sequence variation in ABCG8 are related to plant sterol metabolism in healthy volunteers. J. Lipid Res. 2005, 46, 68-75.
50. Salen, G.; Ahrens, E.H. Jr.; Grundy, S.M. Metabolism of β-sitosterol in man. J. Clin. Invest. 1970, 49, 952-967.
51. Grandgirard, A.; Demaison-Meloche, J.; Cordelet, B.; Demaison, L. Incorporation of oxyphytosterols in tissues of hamster. Reprod. Nutr. Dev. 2004, 44, 609-616.
52. Brooks, C.J.W.; McKenna, R.M.; Cole, W.J.; Maclachlan, J.; Lawric, T.D.V. "Profile" Analysis of oxygenated sterols in plasma and serum. Biochem. Soc. Trans. 1983, 11, 700-701.
53. Plat, J.; Brzezinka, H.; Lutjohann, D.; Mensink, R.P.; von Bergmann, K. Oxidised plant sterols in human serum and lipid infusions as measured by combined gas-liquid chromatography-mass spectrometry. J. Lipid Res. 2001, 42, 2030-2038.
54. 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.
55. Grandgirard, A.; Martine, L.; Juaneda, P.; Cordelet, B. Sitostanetriol is not formed from sitosterol in the rat. Reprod. Nutr. Dev. 2004, 44, 609-616.
56. Tonello, A. Serum phytosterols not only from dietary intake. Br. J. Nutr. 2006, 96, 791-792.
57. Aringer, L. Conversion, of 7α-hydroxycholesterol and 7α-hydroxy-β-sitosterol to 3α,7α-dihydroxy-and 3α,7α,12α-trihydroxy-5β-steroids in vitro. J. Lipid Res. 1975, 16, 426-433.
58. Maerker, G.; Nungesser, E.H.; Bunick, F.J. Reaction of cholesterol 5, 6-epoxides with stimulated gastricjui.ee. Lipids 1988, 23, 761-765.
59. Lyons, M.A.; Samman, S.; Gatto, L.; Brown, A.J. Rapid hepatic metabolism of an oxysterol, 7-ketocholesterol in vivo: implications for dietary oxysterols. J. Lipid Res. 1999, 40, 1846-18457.
60. Larsson, H.; Bottiger, Y.; Iuliano, L.; Diczfalusy, U. In vivo interconversion of 7β-hydroxycholesterol and 7-ketocholesterol, potential surrogate markers for oxidative stress. Free Radic. Biol. Med. 2007, 43, 695-701.
61. Brown, A.J.; Watts, G.F.; Burnett, J.R.; Dean, R.T.; Jessup, W. Sterol 27 hydroxylase acts on 7-ketocholesterol in human atherosclerotic lesions and macrophages in culture. J. Biol. Chem. 2000, 275, 27627-27633.
62. Lyons, M.A.; Brown, A.J. Metabolism of an oxysterol, 7-ketocholesterol, by sterol hydroxylase in HepG2 cells. Lipids 2001, 36, 701-711
63. 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.
64. 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. Agri. Food Chem. 2001, 49, 2090-2095.
65. 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.
66. Lea, L.J.; Hepburn, P.A.; Wolfreys, A.M.; Baldrick, P. Safety evaluation of phytosterol esters. Part 8. Lack of genotoxicity and subchronic toxicity with phytosterol oxides. Food Chem. Toxicol. 2004, 42, 771-783.
67. 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 characteristion of β-sitosterol and β-sitosterol oxide derivatives. Org. Biomol. Chem. 2005, 3, 3059-3065.
68. Ryan, E.; Chopra, J.; McCarthy, F.; Maguire, A.R.; O'Brien, N.M. 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.
69. Lizard, G.; Gueldry, S.; Sordet, O.; Monier, S.; Athias, A.; Miguet, C.; Bessede, G.; Lemaire, S.; Solary, E.; Gambert, P. Glutathione is implied in the control of 7-ketocholesterol-induced apoptosis, which is associated with radical oxygen species production. F.A.S.E.B. J. 1998, 12, 1651-1663.
70. Olkkonen, V.M.; Lehto, M. Oxysterols and oxysterol binding proteins: role in lipid metabolism and atherosclerosis. Ann. Med. 2004, 36, 562-572.
71. Peterson, A.R.; Peterson, H.; Spears, C.P.; Trosko, J.E.; Sevanian, A. Mutagenic characterisation of cholesterol epoxides in Chinese hamster V79 cells. Mutat. Res. 1988, 203, 355-366.
72. Cheng, Y.W.; Kang, J.J.; Shin, Y.L.; Lo, Y.L.; Wang, C.F. Cholesterol-3-beta, 5-alpha, 6-beta-triol induced genotoxicity through reactive oxygen species formation. Food Chem. Toxicol. 2005, 43, 617-622.
73. Abramsson-Zetterberg, L.; Svensson, M.; Johnsson, L. No evidence of genotoxic effect in vivo of the phytosterol oxidation products triols and epoxides. Toxicol. Lett. 2007, 173, 132-139.
74. Christiansion-Heika, I.; Smeds, P.; Granholm, N.; Bergelin, E.; Isomaa, B. Endocrine modulating actions of a phytosterol mixture in zebrafish (Danio rerio). Comp. Biochem. Physiol. C Toxicol. Pharmacol. 2007, 145, 518-527.
75. van den Heuvel, M.R.; Leusch, F.D.; Taylor, S.; Shannon, N.; McKague, A.B. Assessment of the reproductive-endocrine disrupting potential of chlorine dioxide oxidation products of plant sterols. Environ. Sci. Technol. 2006, 40, 2594-2600.
76. Newill, H.; Loske, R.; Wagner, J.; Johannes, C.; Lorenz, R.L.; Lehmann, L.. Oxidation products of stigmasterol interfere with the action of female sex hormone 17β-estradiol in cultured human breast and endometrium cell lines. Mol. Nutr. Food Res. 2007, 57, 888-898.
77. Sato, H.; Nishida, S.; Tomoyori, H.; Sato, M.; Ikeda, I.; Imaizumi, K. Oxysterol regulation of estrogen receptor a-mediated gene expression in a transcriptional activation assay system using HeLa cells. Biosci. Biotechnol. Biochem. 2004, 68, 1790-1793.
78. Pakrashi, A.; Basak, B. Abortifacient effect of steroids from ananas comosus and their analogues on mice. J. Reprod. Fertil. 1976, 46, 461-462.
79. Ikeda, I.; Konno, R.; Shimizu, T.; Ide, T.; Takahashi, N.; Kawada, T. Campest-5-en-3-one, an oxidised derivative of campesterol, activates PPARalpha, promotes energy consumption and reduces visceral, fat deposition in rats. Biochim. Biophys. Acta 2006, 1760, 800-807.
80. Suzuki, K.; Tanaka, M.; Konno, R.; Kaneko, Y. Effects of 5-campestenone (24-methylcholest-5-en-3-one) on the type 2 diabetes mellitus model animal C57BL/KsJ-db/db mice. Horm. Metab. Res. 2002, 34, 121-126.
81. Duta, P.C.; Savage, G.P. Formation and content of phytosterol oxidation products in foods. In Cholesterol and Phytosterol Oxidation Products: Analysis, Occurrence and Biological Effects, Guardiola, F.; Dutta, P.C.; Codony, R.; Savage, G.P.; Eds.; AOCS Press: Champaign, IL, 2002; 319-334.