Fisheries Science

, Volume 73, Issue 4, pp 897–901 | Cite as

Effects of reactive radicals and heat on trans-isomerization of eicosapentaenoic acid

  • Nobuhiro Zaima
  • Tatsuya Sugawara
  • Yuki Otsubo
  • Takashi Hirata
Article

Abstract

Trans geometric isomers of eicosapentaenoic acid (TEPA) have been found as minor components in human platelets. However, there is little information on the mechanism of trans-isomerization of eicosapentaenoic acid (EPA) in vitro and in vivo. The effects of reactive radicals and heat on trans-isomerization of EPA were examined. Trans-isomerization occurred when EPA ethyl ester reacted with nitrogen dioxide radical (NO2) but not with 2,2′-azobis(2,4-dimethylvaleronitrile). TEPA was also produced from EPA ethyl ester heated at 200°C for 60 h. No TEPA, however, was detected in sardines Sardinops melanostictus after boiling, roasting, or microwave heating. These results suggest that EPA is trans-isomerized by NO2in vivo while trans-isomerization of EPA does not occur during conventional cooking.

Key Words

conventional cooking eicosapentaenoic acid reactive radicals trans geometric isomers of eicosapentaenoic acid trans-isomerization 

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References

  1. 1.
    Chardigny JM, Wolff RL, Mager E, Bayard CC, Sébédio JL, Martine L, Rantnayake WMN. Fatty acid composition of French infant formulas with emphasis on the content and detailed profile of trans fatty acids. J. Am. Oil. Chem. Soc. 1996: 73: 1595–1601.CrossRefGoogle Scholar
  2. 2.
    Sébédio JL, Grandgirard A, Prevost J. Linoleic acid isomers in heat treated sunflower oils. J. Am. Oil Chem. Soc. 1988; 65: 362–366.CrossRefGoogle Scholar
  3. 3.
    Stender S, Dyerberg J. Influence of trans fatty acids on health. Ann. Nutr. Metab. 2003; 48: 61–66.PubMedCrossRefGoogle Scholar
  4. 4.
    Vermunt SHF, Becaufrère B, Riemersma RA, Sébédio JL, Chardigny JM, Mensink RP. transLinE investigators. Dietary trans a-linolenic acid from deodorized rapeseed oil and plasma lipids and lipoproteins in healthy men: the trans-LinE study. Br. J. Nutr. 2001; 85: 387–392.PubMedCrossRefGoogle Scholar
  5. 5.
    Jiang H, Kruger N, Lahiri DR, Wang D, Vatèle JM, Balazy M. Nitrogen dioxide induces cis-trans-isomerization of arachidonic acid within cellular phospholipids. J. Biol. Chem. 1999; 274: 16235–16241.PubMedCrossRefGoogle Scholar
  6. 6.
    Zock PL, Mattijin BK. Trans fatty acids, lipoproteins, and coronary risk. Can. J. Physiol. Pharmacol. 1997; 75: 211–216.PubMedCrossRefGoogle Scholar
  7. 7.
    Sargis RM, Subbaiah PV. Trans unsaturated fatty acids are less oxidizable than cis unsaturated fatty acids and protect endogenous lipids from oxidation in lipoproteins and lipid bilayers. Biochemistry 2003; 42: 11533–11543.PubMedCrossRefGoogle Scholar
  8. 8.
    Berdeaux O, Chardigny JM, Sébédio JL, Mairot T, Poullain D, Vatèle JM, Noël JP. Effects of a trans isomer of arachidonic acid on rat platelet aggregation and eicosanoid production. J. Lipid Res. 1996; 37: 2244–2250.PubMedGoogle Scholar
  9. 9.
    Chardingny JM, Sébédio JL, Juanéda P, Vatèle JM, Grandgirard A. Occurrence of n-3 trans polyunsaturated fatty acids in human platelets. Nutr. Res. 1993; 13: 1105–1111.CrossRefGoogle Scholar
  10. 10.
    Grandgirard A, Piconneaux A, Sébédio JL, Quére L. Occurrence of geometrical isomers of eicosapentaenoic and docosahexaenoic acids in liver lipids of rats fed heated linseed oil. Lipids 1989; 24: 799–804.PubMedCrossRefGoogle Scholar
  11. 11.
    Loï C, Chardigny JM, Berdeaux O, Vatèle JM, Poullain D, Noël JP, Sébédio JL. Effects of three trans isomers of eicosapentaenoic acid on rat platelet aggregation and arachidonic acid metabolism. Thromb. Haemost. 1998; 80: 656–661.PubMedGoogle Scholar
  12. 12.
    Zaima N, Sugawara T, Arai H, Nakamura K, Takasugi M, Fukunaga K, Noguchi R, Hirata T. Characterization of trans eicosapentaenoic acid isomers: oxidative stability and antiinflammatory activity. J. Oleo Sci. 2005; 54: 505–512.Google Scholar
  13. 13.
    Bligh EG, Dyer WJ. A rapid method of total lipid extraction and purification. Can. J. Biochem. 1959; 37: 911–917.PubMedCrossRefGoogle Scholar
  14. 14.
    Craig BM, Murty NL. Quantitative fatty acid analysis of vegetable oils by gas-liquid chromatography. J. Am. Oil Chem. Soc. 1959; 36: 549–552.CrossRefGoogle Scholar
  15. 15.
    Porter NA, Lehman LS, Weber BA, Smith KJ. Unified mechanism for polyunsaturated fatty acid autoxidation. Competition of peroxy radical hydrogen atom abstraction, β-scission, and cyclization. J. Am. Chem. Soc. 1981; 103: 6447–6455.CrossRefGoogle Scholar
  16. 16.
    Zghibech CM, Gopal VR, Poff CD, Falck JR, Balazy M. Determination of trans-arachid onic acid isomers in human blood plasma. Anal. Biochem. 2004; 332: 137–144.CrossRefGoogle Scholar

Copyright information

© The Japanese Society of Fisheries Science 2007

Authors and Affiliations

  • Nobuhiro Zaima
    • 1
  • Tatsuya Sugawara
    • 1
  • Yuki Otsubo
    • 1
  • Takashi Hirata
    • 1
  1. 1.Division of Applied Biosciences, Graduate School of AgricultureKyoto UniversityKyotoJapan

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