A novel chiral stationary phase LC-MS/MS method to evaluate oxidation mechanisms of edible oils

Junya Ito, Naoki Shimizu, Eri Kobayashi, Yasuhiko Hanzawa, Yurika Otoki, Shunji Kato, Takafumi Hirokawa, Shigefumi Kuwahara, Teruo Miyazawa, Kiyotaka Nakagawa

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)


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.

Original languageEnglish
Article number10026
JournalScientific reports
Issue number1
Publication statusPublished - 2017 Dec 1

ASJC Scopus subject areas

  • General


Dive into the research topics of 'A novel chiral stationary phase LC-MS/MS method to evaluate oxidation mechanisms of edible oils'. Together they form a unique fingerprint.

Cite this