Development of a quantitative method for analyzing three imidazole dipeptides using high-performance liquid chromatography and its application for meat and fish

Hiemori-Kondo, Miki; Shinya, Daisuke; Ueta, Rena

doi:10.1016/j.jfca.2021.104323

Cited by 6 publications

(4 citation statements)

References 42 publications

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“…High levels of His were detected in the tuna (5.29 mmol/100 g-wet) and skipjack tuna (9.78 mmol/100 g-wet) samples ( Table S5 and Figure 6 e). This is consistent with reports that black marlin [ 57 ], yellowfin tuna [ 40 , 58 , 59 ], and skipjack tuna [ 47 , 57 , 59 , 60 ] contain high levels of His. Nimura et al, speculated that the high concentration of His in the muscles of tuna, which swim explosively, is due to the pH buffering capacity of His, which is inferior to that of IDPs [ 61 ].…”

Section: Resultssupporting

confidence: 92%

“…Specifically, they were higher than those achieved by Pandya et al by electrospray ionization (ESI)–MS/MS using a heated ESI probe [ 29 ]; comparable to those obtained by Uenoyama et al, Stautemas et al, and Peiretti et al using ESI–MS/MS [ 28 , 30 , 34 ], and lower than those determined by Everaert et al by ESI–MS/MS using a heated ESI probe [ 33 ] ( Table 2 ). Moreover, the LOD was several orders of magnitude lower than those of other methods, including ultraviolet detection with different columns (e.g., with a C18 column [ 35 , 36 ], hydrophilic interaction LC column [ 37 , 38 ], Hypercarb TM column [ 39 ], and amino column [ 40 ]) and fluorescence detection [ 41 ] ( Table 2 ). These results suggest that the derivatization of Car and Ans with ( R )-CIMa-OSu allows the simultaneous analysis of all relevant amino acids and Tau in seafoods, with comparative LODs to previous papers, even when only small amounts (<200 mg) of sample are available.…”

Section: Resultsmentioning

confidence: 99%

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Determination of Imidazole Dipeptides and Related Amino Acids in Natural Seafoods by Liquid Chromatography–Tandem Mass Spectrometry Using a Pre-Column Derivatization Reagent

Onozato,

Horinouchi,

Yoshiba

et al. 2024

Foods

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Imidazole dipeptides (IDPs) and taurine (Tau) have several health benefits and are known to be contained in natural seafoods. However, their levels vary widely in different natural seafoods, making their simultaneous determination desirable. Herein, we employ a liquid chromatography–tandem mass spectrometry approach using a novel amino group derivatization reagent, succinimidyl 2-(3-((benzyloxy)carbonyl)-1-methyl-5-oxoimidazolidin-4-yl) acetate ((R)-CIMa-OSu), for the simultaneous quantification of IDPs (carnosine (Car) and anserine (Ans)), their related amino acids, and Tau in natural seafoods. Each seafood sample contained different concentrations of IDPs (Car: ND to 1.48 mmol/100 g-wet, Ans: ND to 4.67 mmol/100 g-wet). The Car levels were considerably higher in eel, while Tau was more abundant in squid, boiled octopus, and scallop. Thus, the derivatization reagent (R)-CIMa-OSu provides a new approach to accurately assess the nutritional composition of seafoods, thereby providing valuable insight into its dietary benefits.

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Section: Resultssupporting

confidence: 92%

Section: Resultsmentioning

confidence: 99%

Determination of Imidazole Dipeptides and Related Amino Acids in Natural Seafoods by Liquid Chromatography–Tandem Mass Spectrometry Using a Pre-Column Derivatization Reagent

Onozato,

Horinouchi,

Yoshiba

et al. 2024

Foods

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“…In addition, our study also showed differences in anserine. Anserine is a dipeptide found as an abundant non-protein nitrogen-containing compound [37]. It is reported to have a significant effect on muscle functions, such as pH buffering ability, antioxidant capacity, and increased Ca 2+ sensitivity; these previous studies are consistent with our results [34].…”

Section: Discussionsupporting

confidence: 91%

Biomarker Development for Identifying Mud Loach (Misgurnus mizolepis) Origin Country Using Untargeted Metabolite Profiling

Kim,

Shin,

Yang

et al. 2023

Life

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Mud loach (Misgurnus mizolepis) has long been consumed in Korea. Recently, Chinese mud loaches were replaced with expensive Korean mud loaches, owing to taste and preference. Such issues occur in aquatic food distribution processes, leading to inferior food delivery. Previously, a study was conducted to confirm the origin of mud loaches using genetic analysis. However, untargeted metabolites profiling of mud loaches has not been reported. Untargeted metabolomics provides information on the overall metabolic profiling of a sample, allowing the identification of new metabolites. Here, we analyzed the metabolites of mud loaches of different geographical origins using liquid chromatography (LC)-quadrupole-time-of-flight mass spectrometry (MS). Orthogonal partial least squares discriminant analysis from LC/MS datasets showed a clear distinction between Korean and Chinese mud loaches, and univariate statistical analysis showed significantly different metabolites between them. N-acetylhistidine and anserine were selected as biomarkers for geographical origin discrimination using the receiver operating characteristic curve. N-acetylhistidine and anserine levels were significantly higher in Chinese than in Korean mud loaches. These results indicate that metabolic analysis can be used to discriminate between the geographical origins of mud loaches, curtailing the inadvertent substitution of mud loaches from different regions.

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“…Numerous studies have demonstrated the detection and quantification of IDPs using HPLC coupled with various detection systems, such as ultraviolet (UV) detectors [ 26 , 27 ] and fluorescence detectors [ 28 , 29 ]. Furthermore, HPLC coupled with MS/MS has also been applied for the detection and quantitation of IDPs [ 30 ].…”

Section: Introductionmentioning

confidence: 99%

Quantitative Determination of 2-Oxo-Imidazole-Containing Dipeptides by High-Performance Liquid Chromatography/Tandem Mass Spectrometry

et al. 2022

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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.

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Development of a quantitative method for analyzing three imidazole dipeptides using high-performance liquid chromatography and its application for meat and fish

Cited by 6 publications

References 42 publications

Determination of Imidazole Dipeptides and Related Amino Acids in Natural Seafoods by Liquid Chromatography–Tandem Mass Spectrometry Using a Pre-Column Derivatization Reagent

Determination of Imidazole Dipeptides and Related Amino Acids in Natural Seafoods by Liquid Chromatography–Tandem Mass Spectrometry Using a Pre-Column Derivatization Reagent

Biomarker Development for Identifying Mud Loach (Misgurnus mizolepis) Origin Country Using Untargeted Metabolite Profiling

Quantitative Determination of 2-Oxo-Imidazole-Containing Dipeptides by High-Performance Liquid Chromatography/Tandem Mass Spectrometry

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