cis-trans-isomerization of unsaturated fatty acids during γ-irradiation of barley grains

Radiation Physics and Chemistry

Volumn 67, Issue 2, 2003, Pages 105-113

  Geißler, Christian ^a   Brede, Ortwin ^a   Reinhardt, Jürgen ^b  

^a UNIVERSITY OF LEIPZIG   (Germany)

^b LEIBNIZ INSTITUTE OF SURFACE ENGINEERING IOM   (Germany)

Author keywords

Barley grains; cis trans Isomerization; Gamma irradiation; Thiyl radicals; Unsaturated fatty acids

Indexed keywords

GAMMA RAYS; GRAIN (AGRICULTURAL PRODUCT); IRRADIATION; ISOMERIZATION; UNSATURATED COMPOUNDS;

DOSE DEPENDENT ISOMERIZATION;

OLEIC ACID;

LINOLEIC ACID; LINOLENIC ACID; NATURAL PRODUCT; OLEIC ACID; UNSATURATED FATTY ACID; VACCENIC ACID;

ARTICLE; BARLEY; BUTTER; CIS TRANS ISOMERISM; FATTY ACID ANALYSIS; FOOD ANALYSIS; FOOD IRRADIATION; FOOD SAFETY; GAMMA IRRADIATION; NUTRITION; RADIATION DOSE;

BARLEY; GAMMA RAYS; ISOMERIZATION; OLEIC ACID; RADIATION EFFECTS;

EID: 18344413607     PISSN: 0969806X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0969-806X(03)00003-3     Document Type: Article

References (37)

1. Adhikari S., Sprinz H., Brede O. Thiyl radical induced isomerization of unsaturated fatty acids. determination of equilibrium constants for this catalytical process Res. Chem. Intermed. 27:2001;549-559.
2. Allison D.B., Egan S.K., Barraj L.M., Caughman C., Infante M., Heimbach J.T. Estimated intake of trans fatty and other fatty acids in the US population. J. Am. Diet. Assoc. 99(2):1999;166-174.
3. Ammon J., Mildau G., Ruge W., Delincée H. Nachweis einer Bestrahlung von Hühnerfleisch durch gaschromatographische Messung von Radiolyseprodukten aus der Fettfraktion. Dtsch. Lebensm.-Rundsch. 88:1992;35-42.
4. Bakker N., Van't Veer P., Zock P.L. Adipose fatty acids and cancers of the breast, prostata and colon. an ecological study Int. J. Cancer. 72(4):1997;587-591.
5. Balboni J.J., Nawar W.W. Apparatus for direct collection of volatiles from meat. J. Agric. Food Chem. 18:1970;746-752.
6. Cesano A., Visonneau S., Scimeca J.A., Kritchevsky D., Santoli D. Opposite effects of linoleic acid and conjugated linoleic acid on human prostatic cancer in SCID mice. Anticancer Res. 18(3A):1998;1429-1434.
7. Chatgilialoglu Ch., Ferreri C., Ballestri M., Mulazzani Q.G., Landi L. cis-trans-Isomerization of monounsaturated fatty acid residues in phospholipids catalyzed by thiyl radicals. J. Am. Chem. Soc. 122:2000;4593-4601.
8. Dalhelm, H., Geiβler, C., Graubner, L., Gropp, J., Fürll, M., Kirbach, H., Winkler, C., Reinacher, M., Bellmann, S., Richter, V., Rassuol, F., Lösch, U., Erhard, M., Bögl, K.W., Schreiber, G., Schulzki, G., 1997. Untersuchungen zur Auswirkung der Fütterung von bestrahlter Gerste auf hämatologische und Lipidstoffwechsel-Parameter wachsender Wachteln und Ratten. Report of Bundesministerium für Gesundheit No. 4414-6080-4/22, Berlin, 1997.
9. Ferreri C., Costantino C., Landi L., Mulazzani Q.G., Chatgilialoglu Ch. The thiyl radical mediated isomerization of cis-monounsaturated fatty acid residues in phospholipids. a novel path of membrane damage Chem. Commun. 1999:1999;407-408.
10. Fricke H., Hart E.J. The ferrous sulfate dosimeter. Attix F.H., Roesch W.C. Radiation Dosimetry. Vol. 2:1966;Academic Press, New York. (Chapter 12).
11. Gunstone, F.D., Harwood, J.L., Padley, F.B., 1994. The Lipid Handbook, 2nd Edition. Chapman & Hall, London, Glasgow, Weinheim, New York, Tokyo, Melbourne, Madras.
12. Hulshof K.F. Intake of fatty acids in Western Europe with emphasis on trans fatty acids. the TRANSFAIR Study Eur. J. Clin. Nutr. 53(2):1999;143-157.
13. Ip C. Review of the effects of trans fatty acids, oleic acid, n-3 polyunsaturated fatty acids, and conjugated linoleic acid on mammary carcinogenesis in animals. Am. J. Clin. Nutr. 66:1997;1523-1529.
14. Ip C., Scimeca J.A. Conjugated linoleic acid and linoleic acid are distinctive modulators of mammary carcinogenesis. Nutr. Cancer. 27(2):1997;131-135.
15. Judd J.T., Baer D.J., Clevidence B.A., Muensing R.A., Chen S.C., Westrate J.A., Meijer G.W., Wittes J., Lichtenstein A.H., Vilella-Bach M., Schaefer E.J. Effects of margarine compared with those of butter on blood lipid profiles related to cardiovascular disease risk factors in normolipemic adults fed controlled diets. Am. J. Clin. Nutr. 68(4):1988;768-777.
16. Kovacs, A., Stenger, V., Földiak, G., Legeze, L., 1985. High-Dose Dosimetry. IAEA, Vienna, p. 135.
17. Lück H., Kohn Einwirkung ionisierender Strahlung auf Fette. cis-trans-Isomerisierung und Verschiebung der Doppelbindungen Nahrung. 7:1963;199-211.
18. Mosley E.E., Powell G.L., Riley M.B., Jenkins T.C. Microbial biohydrogenation of Oleic acid to trans isomers in vitro. J. Lipid Res. 43(2):2002;290-296.
19. Naumann C., Bassler R. Methodenbuch Band III, Die chemische Untersuchung von Futtermitteln. 1997;VDLUFA-Verlag, Darmstadt. (Chapter 5.1.1).
20. Nawar, W.W., 1994. Progress in the detection of irradiated foods by measurement of lipid-derived volatiles. 3. FAO/IAEA Research Co-ordination Meeting on Analytical Detection Methods for Irradiation Treatment of Foods (ADMIT) Belfast, Northern Ireland, 20-24 June 1994.
21. Nelson G.J. Dietary fat, trans fatty acids, and risk of coronary heart disease. Nutr. Rev. 56(8):1998;250-252.
22. O'Shea M., Devery R., Lawless F., Murphy J., Stanton C. Milk fat conjugated linoleic acid (CLA) inhibits growth of human mammary MCF-7 cancer cells. Anticancer Res. 20(5B):2000;3591-3601.
23. Precht D., Molkentin J. Effect of feeding on conjugated cis-Δ-9, trans-Δ-11-octadeca-dienoic acid and other isomers of linoleic acid in bovine milk fat. Nahrung. 41(6):1997;330-335.
24. Rakoff, H., Emken, E.A., 1982. Chem. Phys. Lipids 31, 215-225, cited in: Christie, W.W., Gas Chromatography and Lipids. The oily press, Ayr, Scotland, 1982, p. 105.
25. Reinhardt J., Remer M., Bär M. Design, evaluation and handling of gamma irradiators-10 years of PANORAMA unit operation. Isotopenpraxis. 23:1987;442-446.
26. Schreiber, G.A., Schulzki, A., 1993. Gas chromatographic analysis of volatile hydrocarbons to detect irradiated chicken, pork and beef - an intercomparison study. Report of the Institut für Sozialmedizin und Epidemiologie des Bundesgesundheitsamtes, Berlin, 1993, ISBN 3-89254-159-0.
27. Schwinn J., Sprinz H., Drößler K., Leistner S., Brede O. Thiyl radical induced cis-trans-isomerization of methyl linoleate in methanol and of linoleic acid residues in liposomes. Int. J. Radiat. Biol. 74:1998;359-365.
28. Sharpio S. Do trans fatty acids increase the risk of coronary artery disease? A critique of the epidemiologic evidence. Am J. Clin. Nutr. 66(4 Suppl.):1997;1011-1017.
29. Slattery M.L., Benson J., Ma K.N., Schaffer D., Potter J.D. trans-Fatty acids and colon cancer. Nutr. Cancer. 39(2):2001;170-175.
30. Sprinz H., Schwinn J., Naumov S., Brede O. Mechanism of thiyl radical catalyzed isomerization of unsaturated fatty acid residues in homogeneous solution and in liposomes. Biochim. Biophys. Acta. 1483:2000;91-100.
31. Sprinz H., Adhikari S., Brede O. Transformation of phospholipid membranes by thiyl radicals via cis-trans isomerization of fatty acid residues. Adv. Colloid Interface Sci. 89-90:2001;313-325.
32. Stanton C., Lawless F., Kjellmer G., Harrington D., Devery R., Connolly J.F., Murphy J. Dietary influence on bovine milk cis-9, trans-11-conjugated linoleic acid content. J. Food Sci. 62:1997;1083-1086.
33. Tavani A., Negri E., D'Avanzo B., La Vecchia C. Margarine intake and risk of nonfatal acute myocardial infarction in Italian women. Eur. J. Clin. Nutr. 51(1):1997;30-32.
34. Vaca C.E., Harms-Ringdahl M. Radiation-induced lipid peroxidation in whole grain of rye, wheat and rice. effects on linoleic and linolenic acid Radiat. Phys. Chem. 43:1986;49-62.
35. van de Vijver L.P., Kardinaal A.F., Couet C., Aro A., Kafatos A., Steingrimsdottir L., Amorim Cruz J.A., Moreiras O., Becker W., van Amelsvoort J.M., Vidal-Jessel S., Salminen I., Moschandreas J., Sigfusson N., Martins I., Carbajal A., Ytterffors A., Poppel G. Association between trans fatty acid intake and cardiovascular risk factors in Europe. the TRANSFAIR study Eur. J. Clin. Nutr. 54(2):2000;126-135.
36. Woidich H. Über die praktische Durchführung gaschromatographischer Analysen auf dem Fettgebiet. Z. Lebensm.-Unters. Forsch. 129(4):1966;197-205.
37. Zock P.L., Urgert R., Hulshof P.J., Katan M.B. Transvertzuren in de voeding. risico op coronaire hartziekten Ned. Tijdschr. Geneeskd. 142(30):1998;1701-1704.