Formation of fluorescent substances from degradation products of methyl linoleate hydroperoxides with amino compound.

The degradation products formed from methyl linoleate hydroperoxides by reaction with heme were fractionated by Sephadex LH-20 column chromatography and by reverse-phase high performance liquid chromatography, and the ability of each compound to form fluorescent substances through reaction with amino compound was compared. Maximum formation of fluorescent substances was obtained from monomeric degradation products with amino compound, but low molecular weight aldehydes such as hexanal, 2-hexenal and 2,4-decadienal, formed only a small amount of fluorescent substances. However, the major monomeric degradation products described previously, the hydroxy-, keto- and epoxy-derivatives, do not significantly contribute to the formation of fluorescent substances through reaction with amino compound. It was suggested that formation of fluorescent substances from lipid peroxides with amino compound may originate from a precursor present in monomeric degradation products formed from hydroperoxide of methyl linoleate during lipid peroxidation, and that low molecular weight aliphatic aldehydes are not involved in fluorescent substance formation. Moreover, the majority of TBA-reactive substances in secondary oxidation products prepared from autoxidized methyl linoleate are also unrelated to the formation of fluorescent substances through reaction with amino compound.