Products formed during thermo-oxidative degradation of phytosterols

JAOCS, Journal of the American Oil Chemists' Society

Volumn 86, Issue 7, 2009, Pages 651-662

  Rudzińska, Magdalena ^a   Przybylski, Roman ^b   Wąsowicz, Erwin ^a  

^a POZNA UNIVERSITY OF LIFE SCIENCES   (Poland)

^b UNIVERSITY OF LETHBRIDGE   (Canada)

Author keywords

Campestanol; Campesterol; GC MS; Heating; HPSEC; Off flavor compounds; Oligomers; Oxyphytosterols; Sitostanol; Sitosterol

Indexed keywords

ALCOHOLS; HEATING; LIPIDS; OLIGOMERS; OXIDATION; VOLATILE ORGANIC COMPOUNDS;

CAMPESTANOL; CAMPESTEROL; GC/MS; HPSEC; OXYPHYTOSTEROLS; SITOSTANOL; SITOSTEROL;

FLAVOR COMPOUNDS;

EID: 67650066530     PISSN: 0003021X     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11746-009-1397-0     Document Type: Article

References (37)

1. Smith LL (1981) Cholesterol autoxidation. Plenum, New York
2. M Rudzińska T Kazuś E Wa̧sowicz 2001 Sterols and their oxidized derivatives in refined and cold pressed seed oils Rosl Oleiste 22 477 494
3. Moreau RA (2004) Plant sterols in functional foods. In: Dutta PC (ed) Phytosterols as functional food components and nutraceuticals. Marcel Dekker, New York, pp 317-345
4. A-M Lampi L Juntunen J Toivo V Piironen 2002 Determination of thermo-oxidation products of plant sterols J Chrom B 777 83 92 (Pubitemid 35264605)
5. Rudzińska M, Jeleń H, Wa̧sowicz E (2002) The content of phytosterols and their oxidized derivatives in heated plant oils. Pol J Food Nutr Sci 11/52SI1:129-134 (Pubitemid 36385991)
6. WB Zhang PB Addis TP Krick 1991 Quantification of 5α-cholestane- 3β, 5, 6β-triol and other cholesterol oxidation products in fast food French fried potatoes Pol J Food Nutr Sci 56 716 718
7. PC Dutta 1997 Studies on phytosterol oxides. II. Content in some vegetable oils and in French fries prepared in these oils JAOCS 74 659 666 (Pubitemid 127672348)
8. PC Dutta LÅ Appelqvist 1997 Studies on phytosterol oxides. I. Effect of storage on the content in potato chips prepared in different vegetable oils JAOCS 74 647 657 (Pubitemid 127672347)
9. Przybylski R, Eskin NAM (1991) Formation of phytosterol oxides in fried oil products. In: McGregor DI (ed) Proceedings of the 8th international rapeseed congress. GCRIC, Saskatoon, pp 888-893
10. M Rudzińska H Jeleń M Nogala-Kałucka M Gawrysiak-Witulska 2006 The influence of storage time and drying temperature on the sterols content in rapeseed Rosl Oleiste 27 345 356
11. R Bortolomeazzi F Cordaro L Pizzale LS Conte 2003 Presence of phytosterols oxides in crude vegetable oils and their fare during refining J Agric Food Chem 51 2394 2401
12. X Zhang D Julien-David M Miesch P Geoffroy F Raul S Roussi D Aoudé-Werner E Marchioni 2005 Identification and quantitative analysis of β-sitosterol oxides in vegetable oils by capillary gas chromatography-mass spectrometry Steroids 70 896 906 (Pubitemid 41564068)
13. M Rudzińska J Korczak E Wa̧sowicz 2005 Changes in phytosterols and their oxidation products during frying of French fries in rapeseed oil Pol J Food Nutr Sci 14/55 4 381 387
14. L Johnsson PC Dutta 2006 Determination of phytosterol oxides in some food products by using an optimized transesterification method Food Chem 97 606 613 (Pubitemid 43185886)
15. A Grandgirard L Martine C Joffre P Juanéda O Berdeaux 2004 Gas chromatographic separation and mass spectrometric identification of mixture of oxyphytosterol and oxycholesterol derivatives. Application to a phytosterol-enriched food J Chrom A 1040 239 250 (Pubitemid 38681038)
16. A Jong J Plat RP Mensink 2003 Metabolic effects of plant sterols and stanols (Review) J Nutr Biochem 14 362 369 (Pubitemid 36952655)
17. KB Hicks RA Moreau 2001 Phytosterol and phytostanols: functional food cholesterol busters Food Technol 55 63 67
18. AB Awad CS Fink 2000 Phytosterols as anticancer dietary components. Evidence and mechanism of action J Nutr 130 2127 2130 (Pubitemid 30682727)
19. AB Awad RL Von Holtz JP Cone CS Fink YC Chen 1998 Beta-sitosterol inhibits growth of HT-29 human colon cancer cells by activating the sphingomyelin cycle Anticancer Res 18 471 473 (Pubitemid 28174751)
20. C Adcox L Boyd L Oehrl J Allen G Fenner 2001 Comparative effects of phytosterol oxides and cholesterol oxides in cultured macrophage-derived cell lines J Agric Food Chem 49 2090 2095
21. W Meyer H Jungnickel M Jandke K Dettner G Spiteller 1998 On the cytotoxicity of oxidized phytosterols isolated from photoautotrophic cell cultures of Chenopodium rubrum tested on meal-worms Tenebrio molitor Phytochemistry 47 789 797 (Pubitemid 28136885)
22. E Hovenkamp I Demonty J Plat D Lütjohann RP Mensink EA Trautwein 2008 Biological effect of oxidized phytosterols: a review of current knowledge Prog Lipid Res 47 37 49 (Pubitemid 350216621)
23. WW Nawar SK Kim YJ Li M Vajdi 1991 Measurement of oxidative interaction of cholesterol JAOCS 68 496 498
24. SK Kim WW Nawar 1993 Parameters influencing cholesterol oxidation Lipids 28 917 922 (Pubitemid 23297122)
25. Lercker G, Rodrigues-Estrada MT (2002) Cholesterol oxidation mechanism. In: Guardiola F, Dutta PC, Codony R, Savage GP (eds) Cholesterol and phytosterol oxidation products. AOCS Press, Champaigne, pp 1-25
26. HH Jeleń M Obuchowska R Zawirska-Wojtasiak E Wa̧sowicz 2000 Headspace solid-phase microextraction use for the characterization of volatile compounds in vegetable oils of different sensory quality J Agric Food Chem 48 2360 2367 (Pubitemid 30431240)
27. ISO/FDIS 16931-2009: Animal and vegetable fats and oils: determination of polymerized triglycerides content by high-performance size-exclusion chromatography (HPSEC)
28. LL Oehrl AP Hansen CA Rohrer GP Fenner LC Boyd 2001 Oxidation of phytosterols in a test food system JAOCS 78 1073 1078 (Pubitemid 34129771)
29. Przybylski R, Zambiazi R, Li W (1999) Kinetics of sterols changes during storage and frying of canola oils. In: Proceedings of the 10th international rapeseed congress, Canberra, Australia, 26-29 September 1999
30. L Soupas L Huikko A-M Lampi V Piironen 2007 Pan-frying may induce phytosterol oxidation Food Chem 101 286 297
31. L Soupas L Juntunen A-M Lampi V Piironen 2004 Effects of sterol structure, temperature, and lipid medium on phytosterol oxidation J Agric Food Chem 52 6485 6491
32. L Soupas L Huikko A-M Lampi V Piironen 2005 Esterification affects phytosterol oxidation Eur J Lipid Sci Technol 107 107 118 (Pubitemid 40450259)
33. http://www.anpro.com/support/MSDS.pdf. Accessed Jan 2009
34. Punderson JO (1958) Manufacture of diketones. US Patent 2,822,389
35. JE van Lier AL da Costa LL Smith 1975 Cholesterol autoxidation identification of the volatile fragments Chem Phys Lipids 14 327 335
36. Dobarganes MC, Márquez-Ruiz G (1996) Dimeric and higher oligomeric triglycerides. In: Perkins EG, Erickson MD (eds) Deep frying. Chemistry, nutrition, and practical applications. AOCS Press, Champaigne, pp 89-111
37. CW Byrdwell WE Neff 2004 Electrospray ionization MS of High M.W. TAG oligomers JAOCS 81 14 26