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A novel chiral stationary phase LC-MS/MS method to evaluate oxidation mechanisms of edible oils
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...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5577281/ https://www.ncbi.nlm.nih.gov/pubmed/28855636 http://dx.doi.org/10.1038/s41598-017-10536-2 |
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author | Ito, Junya Shimizu, Naoki Kobayashi, Eri Hanzawa, Yasuhiko Otoki, Yurika Kato, Shunji Hirokawa, Takafumi Kuwahara, Shigefumi Miyazawa, Teruo Nakagawa, Kiyotaka |
author_facet | Ito, Junya Shimizu, Naoki Kobayashi, Eri Hanzawa, Yasuhiko Otoki, Yurika Kato, Shunji Hirokawa, Takafumi Kuwahara, Shigefumi Miyazawa, Teruo Nakagawa, Kiyotaka |
author_sort | Ito, Junya |
collection | PubMed |
description | 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. |
format | Online Article Text |
id | pubmed-5577281 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-55772812017-09-06 A novel chiral stationary phase LC-MS/MS method to evaluate oxidation mechanisms of edible oils Ito, Junya Shimizu, Naoki Kobayashi, Eri Hanzawa, Yasuhiko Otoki, Yurika Kato, Shunji Hirokawa, Takafumi Kuwahara, Shigefumi Miyazawa, Teruo Nakagawa, Kiyotaka Sci Rep Article 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. Nature Publishing Group UK 2017-08-30 /pmc/articles/PMC5577281/ /pubmed/28855636 http://dx.doi.org/10.1038/s41598-017-10536-2 Text en © The Author(s) 2017 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/. |
spellingShingle | Article Ito, Junya Shimizu, Naoki Kobayashi, Eri Hanzawa, Yasuhiko Otoki, Yurika Kato, Shunji Hirokawa, Takafumi Kuwahara, Shigefumi Miyazawa, Teruo Nakagawa, Kiyotaka A novel chiral stationary phase LC-MS/MS method to evaluate oxidation mechanisms of edible oils |
title | A novel chiral stationary phase LC-MS/MS method to evaluate oxidation mechanisms of edible oils |
title_full | A novel chiral stationary phase LC-MS/MS method to evaluate oxidation mechanisms of edible oils |
title_fullStr | A novel chiral stationary phase LC-MS/MS method to evaluate oxidation mechanisms of edible oils |
title_full_unstemmed | A novel chiral stationary phase LC-MS/MS method to evaluate oxidation mechanisms of edible oils |
title_short | A novel chiral stationary phase LC-MS/MS method to evaluate oxidation mechanisms of edible oils |
title_sort | novel chiral stationary phase lc-ms/ms method to evaluate oxidation mechanisms of edible oils |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5577281/ https://www.ncbi.nlm.nih.gov/pubmed/28855636 http://dx.doi.org/10.1038/s41598-017-10536-2 |
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