TY - JOUR
T1 - A novel chiral stationary phase LC-MS/MS method to evaluate oxidation mechanisms of edible oils
AU - Ito, Junya
AU - Shimizu, Naoki
AU - Kobayashi, Eri
AU - Hanzawa, Yasuhiko
AU - Otoki, Yurika
AU - Kato, Shunji
AU - Hirokawa, Takafumi
AU - Kuwahara, Shigefumi
AU - Miyazawa, Teruo
AU - Nakagawa, Kiyotaka
N1 - Funding Information:
This work was supported in part by JSPS KAKENHI Grant Number 25252025 and 16818703.
Publisher Copyright:
© 2017 The Author(s).
PY - 2017/12/1
Y1 - 2017/12/1
N2 - The elucidation of lipid oxidation mechanisms of food is vital. In certain lipids, characteristic lipid hydroperoxide isomers are formed by different oxidation mechanisms (i.e., photo-oxidation or auto-oxidation). For example, linoleic acid is photo-oxidized to 13-9Z, 11E-hydroperoxyoctadecadienoic acid (HPODE), 12-9Z,13E-HPODE, 10-8E,12Z-HPODE and 9-10E,12Z-HPODE, whereas 13-9Z, 11E-HPODE, 13-9E,11E-HPODE, 9-10E,12Z-HPODE and 9-10E,12E-HPODE are formed by auto-oxidation. Therefore, we considered that oxidation mechanisms could be evaluated by analyzing these characteristic positional and cis/trans lipid hydroperoxide isomers. In this study, we developed a novel chiral stationary phase LC-MS/MS (CSP-LC-MS/MS) method to analyze the positional and cis/trans isomers of HPODE, with the use of a chiral column and sodium ion. Also, as an application of the method, either light-exposed or heated edible oils were treated with lipase to hydrolyze triacylglycerols. The resultant fatty acids including HPODE isomers were analyzed with the developed method. As a result, HPODE isomers characteristic to photo-oxidation were certainly detected in light-exposed edible oils. On the other hand, in heated edible oils, the HPODE isomers characteristic to auto-oxidation were largely increased. Thus, the combination of the developed CSP-LC-MS/MS method with lipase proves to be a powerful tool to evaluate the involvement and mechanisms of lipid oxidation in the process of food deterioration.
AB - The elucidation of lipid oxidation mechanisms of food is vital. In certain lipids, characteristic lipid hydroperoxide isomers are formed by different oxidation mechanisms (i.e., photo-oxidation or auto-oxidation). For example, linoleic acid is photo-oxidized to 13-9Z, 11E-hydroperoxyoctadecadienoic acid (HPODE), 12-9Z,13E-HPODE, 10-8E,12Z-HPODE and 9-10E,12Z-HPODE, whereas 13-9Z, 11E-HPODE, 13-9E,11E-HPODE, 9-10E,12Z-HPODE and 9-10E,12E-HPODE are formed by auto-oxidation. Therefore, we considered that oxidation mechanisms could be evaluated by analyzing these characteristic positional and cis/trans lipid hydroperoxide isomers. In this study, we developed a novel chiral stationary phase LC-MS/MS (CSP-LC-MS/MS) method to analyze the positional and cis/trans isomers of HPODE, with the use of a chiral column and sodium ion. Also, as an application of the method, either light-exposed or heated edible oils were treated with lipase to hydrolyze triacylglycerols. The resultant fatty acids including HPODE isomers were analyzed with the developed method. As a result, HPODE isomers characteristic to photo-oxidation were certainly detected in light-exposed edible oils. On the other hand, in heated edible oils, the HPODE isomers characteristic to auto-oxidation were largely increased. Thus, the combination of the developed CSP-LC-MS/MS method with lipase proves to be a powerful tool to evaluate the involvement and mechanisms of lipid oxidation in the process of food deterioration.
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U2 - 10.1038/s41598-017-10536-2
DO - 10.1038/s41598-017-10536-2
M3 - Article
C2 - 28855636
AN - SCOPUS:85028605279
VL - 7
JO - Scientific Reports
JF - Scientific Reports
SN - 2045-2322
IS - 1
M1 - 10026
ER -