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


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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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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