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

• Published in: Fisheries science Vol. 73; no. 4; pp. 897 - 901
• Main Authors: Zaima, N.(Kyoto Univ. (Japan)), Sugawara, T, Otsubo, Y, Hirata, T
• Format: Journal Article
• Language: English
• Published: Melbourne, Australia Blackwell Publishing Asia 01.08.2007; Springer Nature B.V
• Subjects: ACIDE EICOSAPENTAENOIQUE; ACIDO EICOSAPENTAENOICO; Acids; conventional cooking; Cooking; Diet; EICOSAPENTAENOIC ACID; Fatty acids; Fish oils; FREE RADICALS; HEAT TREATMENT; Heating; ISOMERISATION; ISOMERIZACION; ISOMERIZATION; Marine; Microwave heating; Nitrogen dioxide; RADICAL LIBRE; RADICALES LIBRES; reactive radicals; SARDINOPS MELANOSTICTUS; TRAITEMENT THERMIQUE; trans geometric isomers of eicosapentaenoic acid; trans‐isomerization; TRATAMIENTO TERMICO
• ISSN: 0919-9268; 1444-2906
• DOI: 10.1111/j.1444-2906.2007.01411.x

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 NO2 in vivo while trans‐isomerization of EPA does not occur during conventional cooking.