Elucidation of decomposition pathways of linoleic acid hydroperoxide isomers by GC-MS and LC-MS/MS

Ruriko Miyazaki; Shunji Kato; Yurika Otoki; Halida Rahmania; Masayoshi Sakaino; Shigeo Takeuchi; Toshiro Sato; Jun Imagi; Kiyotaka Nakagawa

doi:10.1093/bbb/zbac189

Elucidation of decomposition pathways of linoleic acid hydroperoxide isomers by GC-MS and LC-MS/MS

Ruriko Miyazaki, Shunji Kato, Yurika Otoki, Halida Rahmania, Masayoshi Sakaino, Shigeo Takeuchi, Toshiro Sato, Jun Imagi, Kiyotaka Nakagawa

AGR - Agricultural Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Food lipid oxidation provides various volatile compounds involved in food flavor via the decomposition of lipid hydroperoxide (LOOH). This study predicted the pathways which can coherently explain LOOH decomposition focusing on hydroperoxy octadecadienoic acid (HpODE) isomers (9-EZ-HpODE, 9-EE-HpODE, 10-HpODE, 12-HpODE, 13-ZE-HpODE, and 13-EE-HpODE) which are the major LOOH contained in edible oils. Each standard was first prepared and thermally decomposed. Generated volatile and non-volatile compounds were analyzed by GC-MS and LC-MS/MS. The results showed that all HpODE decomposition was based on the factors such as favorable scission, radical delocalization, and cyclization. Interestingly, the formation of 8-HpODE and 14-HpODE were demonstrated during HpODE decomposition. The insights obtained in this study would explain the generation pathways of flavor involved in food quality.

Original language	English
Pages (from-to)	179-190
Number of pages	12
Journal	Bioscience, Biotechnology, and Biochemistry
Volume	87
Issue number	2
DOIs	https://doi.org/10.1093/bbb/zbac189
Publication status	Published - 2023 Jan 24

Keywords

food flavor
isomer
lipid hydroperoxide
mass spectrometry
secondary oxidation products

ASJC Scopus subject areas

Biotechnology
Analytical Chemistry
Biochemistry
Applied Microbiology and Biotechnology
Molecular Biology
Organic Chemistry

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10.1093/bbb/zbac189

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title = "Elucidation of decomposition pathways of linoleic acid hydroperoxide isomers by GC-MS and LC-MS/MS",

abstract = "Food lipid oxidation provides various volatile compounds involved in food flavor via the decomposition of lipid hydroperoxide (LOOH). This study predicted the pathways which can coherently explain LOOH decomposition focusing on hydroperoxy octadecadienoic acid (HpODE) isomers (9-EZ-HpODE, 9-EE-HpODE, 10-HpODE, 12-HpODE, 13-ZE-HpODE, and 13-EE-HpODE) which are the major LOOH contained in edible oils. Each standard was first prepared and thermally decomposed. Generated volatile and non-volatile compounds were analyzed by GC-MS and LC-MS/MS. The results showed that all HpODE decomposition was based on the factors such as favorable scission, radical delocalization, and cyclization. Interestingly, the formation of 8-HpODE and 14-HpODE were demonstrated during HpODE decomposition. The insights obtained in this study would explain the generation pathways of flavor involved in food quality.",

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author = "Ruriko Miyazaki and Shunji Kato and Yurika Otoki and Halida Rahmania and Masayoshi Sakaino and Shigeo Takeuchi and Toshiro Sato and Jun Imagi and Kiyotaka Nakagawa",

note = "Publisher Copyright: {\textcopyright} The Author(s) 2022. Published by Oxford University Press on behalf of Japan Society for Bioscience, Biotechnology, and Agrochemistry.",

year = "2023",

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doi = "10.1093/bbb/zbac189",

language = "English",

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T1 - Elucidation of decomposition pathways of linoleic acid hydroperoxide isomers by GC-MS and LC-MS/MS

AU - Miyazaki, Ruriko

AU - Kato, Shunji

AU - Otoki, Yurika

AU - Rahmania, Halida

AU - Sakaino, Masayoshi

AU - Takeuchi, Shigeo

AU - Sato, Toshiro

AU - Imagi, Jun

AU - Nakagawa, Kiyotaka

N1 - Publisher Copyright: © The Author(s) 2022. Published by Oxford University Press on behalf of Japan Society for Bioscience, Biotechnology, and Agrochemistry.

PY - 2023/1/24

Y1 - 2023/1/24

N2 - Food lipid oxidation provides various volatile compounds involved in food flavor via the decomposition of lipid hydroperoxide (LOOH). This study predicted the pathways which can coherently explain LOOH decomposition focusing on hydroperoxy octadecadienoic acid (HpODE) isomers (9-EZ-HpODE, 9-EE-HpODE, 10-HpODE, 12-HpODE, 13-ZE-HpODE, and 13-EE-HpODE) which are the major LOOH contained in edible oils. Each standard was first prepared and thermally decomposed. Generated volatile and non-volatile compounds were analyzed by GC-MS and LC-MS/MS. The results showed that all HpODE decomposition was based on the factors such as favorable scission, radical delocalization, and cyclization. Interestingly, the formation of 8-HpODE and 14-HpODE were demonstrated during HpODE decomposition. The insights obtained in this study would explain the generation pathways of flavor involved in food quality.

AB - Food lipid oxidation provides various volatile compounds involved in food flavor via the decomposition of lipid hydroperoxide (LOOH). This study predicted the pathways which can coherently explain LOOH decomposition focusing on hydroperoxy octadecadienoic acid (HpODE) isomers (9-EZ-HpODE, 9-EE-HpODE, 10-HpODE, 12-HpODE, 13-ZE-HpODE, and 13-EE-HpODE) which are the major LOOH contained in edible oils. Each standard was first prepared and thermally decomposed. Generated volatile and non-volatile compounds were analyzed by GC-MS and LC-MS/MS. The results showed that all HpODE decomposition was based on the factors such as favorable scission, radical delocalization, and cyclization. Interestingly, the formation of 8-HpODE and 14-HpODE were demonstrated during HpODE decomposition. The insights obtained in this study would explain the generation pathways of flavor involved in food quality.

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KW - lipid hydroperoxide

KW - mass spectrometry

KW - secondary oxidation products

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Elucidation of decomposition pathways of linoleic acid hydroperoxide isomers by GC-MS and LC-MS/MS

Abstract

Keywords

ASJC Scopus subject areas

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