Quantitative Determination of 2-Oxo-Imidazole-Containing Dipeptides by High-Performance Liquid Chromatography/Tandem Mass Spectrometry
2-Oxo-imidazole-containing dipeptides (2-oxo-IDPs), novel imidazole-containing dipeptide (IDP) derivatives, exhibit a much higher antioxidant capacity than that of IDPs. However, quantitative methods have only been developed for IDPs, and methods for the quantitative analysis of 2-oxo-IDPs are neede...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-12-01
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| Series: | Antioxidants |
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| Online Access: | https://www.mdpi.com/2076-3921/11/12/2401 |
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| author | Somei Komae Shingo Kasamatsu Koji Uchida Hideshi Ihara |
| author_facet | Somei Komae Shingo Kasamatsu Koji Uchida Hideshi Ihara |
| author_sort | Somei Komae |
| collection | DOAJ |
| description | 2-Oxo-imidazole-containing dipeptides (2-oxo-IDPs), novel imidazole-containing dipeptide (IDP) derivatives, exhibit a much higher antioxidant capacity than that of IDPs. However, quantitative methods have only been developed for IDPs, and methods for the quantitative analysis of 2-oxo-IDPs are needed. In this study, we developed methods for the quantitative analysis of 2-oxo-IDPs by high-performance liquid chromatography with online electrospray ionization-tandem mass spectrometry (HPLC-ESI-MS/MS) coupled with a stable isotope dilution method. First, we prepared stable isotope-labeled IDP and 2-oxo-IDP standards for MS analyses. Next, using these standards, we established highly sensitive, selective, and absolute quantitative analysis methods for five IDPs and five 2-oxo-IDPs by HPLC-ESI-MS/MS, achieving a limit of detection in the fmol range. Finally, we applied the method to various types of meat, such as beef, pork, chicken, and whale meat, demonstrating the detection of both IDPs and 2-oxo-IDPs. Furthermore, we provide the first evidence for the endogenous production of 2-oxo-balenine in meats. The methods developed in this study enable the detection of trace levels of 2-oxo-IDPs in biological samples and could be helpful for understanding the biological relevance of 2-oxo-IDPs. |
| first_indexed | 2024-03-09T17:23:35Z |
| format | Article |
| id | doaj.art-f631a34eb4f4429eaa1afd1f9c0e7b30 |
| institution | Directory Open Access Journal |
| issn | 2076-3921 |
| language | English |
| last_indexed | 2024-03-09T17:23:35Z |
| publishDate | 2022-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Antioxidants |
| spelling | doaj.art-f631a34eb4f4429eaa1afd1f9c0e7b302023-11-24T12:57:24ZengMDPI AGAntioxidants2076-39212022-12-011112240110.3390/antiox11122401Quantitative Determination of 2-Oxo-Imidazole-Containing Dipeptides by High-Performance Liquid Chromatography/Tandem Mass SpectrometrySomei Komae0Shingo Kasamatsu1Koji Uchida2Hideshi Ihara3Department of Biological Science, Graduate School of Science, Osaka Prefecture University, Osaka 599-8531, JapanDepartment of Biological Science, Graduate School of Science, Osaka Prefecture University, Osaka 599-8531, JapanGraduate School of Agricultural and Life Sciences, The University of Tokyo, Tokyo 113-8657, JapanDepartment of Biological Science, Graduate School of Science, Osaka Prefecture University, Osaka 599-8531, Japan2-Oxo-imidazole-containing dipeptides (2-oxo-IDPs), novel imidazole-containing dipeptide (IDP) derivatives, exhibit a much higher antioxidant capacity than that of IDPs. However, quantitative methods have only been developed for IDPs, and methods for the quantitative analysis of 2-oxo-IDPs are needed. In this study, we developed methods for the quantitative analysis of 2-oxo-IDPs by high-performance liquid chromatography with online electrospray ionization-tandem mass spectrometry (HPLC-ESI-MS/MS) coupled with a stable isotope dilution method. First, we prepared stable isotope-labeled IDP and 2-oxo-IDP standards for MS analyses. Next, using these standards, we established highly sensitive, selective, and absolute quantitative analysis methods for five IDPs and five 2-oxo-IDPs by HPLC-ESI-MS/MS, achieving a limit of detection in the fmol range. Finally, we applied the method to various types of meat, such as beef, pork, chicken, and whale meat, demonstrating the detection of both IDPs and 2-oxo-IDPs. Furthermore, we provide the first evidence for the endogenous production of 2-oxo-balenine in meats. The methods developed in this study enable the detection of trace levels of 2-oxo-IDPs in biological samples and could be helpful for understanding the biological relevance of 2-oxo-IDPs.https://www.mdpi.com/2076-3921/11/12/24012-oxo-imidazole-containing dipeptidesimidazole-containing dipeptidescarnosineanserinebaleninehomocarnosine |
| spellingShingle | Somei Komae Shingo Kasamatsu Koji Uchida Hideshi Ihara Quantitative Determination of 2-Oxo-Imidazole-Containing Dipeptides by High-Performance Liquid Chromatography/Tandem Mass Spectrometry Antioxidants 2-oxo-imidazole-containing dipeptides imidazole-containing dipeptides carnosine anserine balenine homocarnosine |
| title | Quantitative Determination of 2-Oxo-Imidazole-Containing Dipeptides by High-Performance Liquid Chromatography/Tandem Mass Spectrometry |
| title_full | Quantitative Determination of 2-Oxo-Imidazole-Containing Dipeptides by High-Performance Liquid Chromatography/Tandem Mass Spectrometry |
| title_fullStr | Quantitative Determination of 2-Oxo-Imidazole-Containing Dipeptides by High-Performance Liquid Chromatography/Tandem Mass Spectrometry |
| title_full_unstemmed | Quantitative Determination of 2-Oxo-Imidazole-Containing Dipeptides by High-Performance Liquid Chromatography/Tandem Mass Spectrometry |
| title_short | Quantitative Determination of 2-Oxo-Imidazole-Containing Dipeptides by High-Performance Liquid Chromatography/Tandem Mass Spectrometry |
| title_sort | quantitative determination of 2 oxo imidazole containing dipeptides by high performance liquid chromatography tandem mass spectrometry |
| topic | 2-oxo-imidazole-containing dipeptides imidazole-containing dipeptides carnosine anserine balenine homocarnosine |
| url | https://www.mdpi.com/2076-3921/11/12/2401 |
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