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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...

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Autores principales: Ito, Junya, Shimizu, Naoki, Kobayashi, Eri, Hanzawa, Yasuhiko, Otoki, Yurika, Kato, Shunji, Hirokawa, Takafumi, Kuwahara, Shigefumi, Miyazawa, Teruo, Nakagawa, Kiyotaka
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2017
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.
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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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