Analyzing Citramalic Acid Enantiomers in Apples and Commercial Fruit Juice by Liquid Chromatography–Tandem Mass Spectrometry with Pre-Column Derivatization

Optically active citramalic acid (CMA) is naturally present as an acidic taste component in fruits, such as apples. The absolute configuration of CMA in such fruits was investigated by high-performance liquid chromatography–tandem mass spectrometry (LC–MS/MS) following pre-column derivatization with...

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Autores principales: Umino, Maho, Onozato, Mayu, Sakamoto, Tatsuya, Koishi, Mikoto, Fukushima, Takeshi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9959191/
https://www.ncbi.nlm.nih.gov/pubmed/36838544
http://dx.doi.org/10.3390/molecules28041556
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author Umino, Maho
Onozato, Mayu
Sakamoto, Tatsuya
Koishi, Mikoto
Fukushima, Takeshi
author_facet Umino, Maho
Onozato, Mayu
Sakamoto, Tatsuya
Koishi, Mikoto
Fukushima, Takeshi
author_sort Umino, Maho
collection PubMed
description Optically active citramalic acid (CMA) is naturally present as an acidic taste component in fruits, such as apples. The absolute configuration of CMA in such fruits was investigated by high-performance liquid chromatography–tandem mass spectrometry (LC–MS/MS) following pre-column derivatization with a chiral reagent, benzyl 5-(2-aminoethyl)-3-methyl-4-oxoimidazolidine-1-carboxylate. The developed LC–MS/MS method successfully separated the enantiomers of CMA using an octadecylsilica column with a resolution and separation factor of 2.19 and 1.09, respectively. Consequently, the R-form of CMA was detected in the peel and fruit of three kinds of apple at concentrations in the 1.24–37.8 and 0.138–1.033 mg/wet 100 g ranges, respectively. In addition, R- CMA was present in commercial apple juice, whereas no quantity was detected in commercial blueberry, perilla, or Japanese apricot juice.
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spelling pubmed-99591912023-02-26 Analyzing Citramalic Acid Enantiomers in Apples and Commercial Fruit Juice by Liquid Chromatography–Tandem Mass Spectrometry with Pre-Column Derivatization Umino, Maho Onozato, Mayu Sakamoto, Tatsuya Koishi, Mikoto Fukushima, Takeshi Molecules Communication Optically active citramalic acid (CMA) is naturally present as an acidic taste component in fruits, such as apples. The absolute configuration of CMA in such fruits was investigated by high-performance liquid chromatography–tandem mass spectrometry (LC–MS/MS) following pre-column derivatization with a chiral reagent, benzyl 5-(2-aminoethyl)-3-methyl-4-oxoimidazolidine-1-carboxylate. The developed LC–MS/MS method successfully separated the enantiomers of CMA using an octadecylsilica column with a resolution and separation factor of 2.19 and 1.09, respectively. Consequently, the R-form of CMA was detected in the peel and fruit of three kinds of apple at concentrations in the 1.24–37.8 and 0.138–1.033 mg/wet 100 g ranges, respectively. In addition, R- CMA was present in commercial apple juice, whereas no quantity was detected in commercial blueberry, perilla, or Japanese apricot juice. MDPI 2023-02-06 /pmc/articles/PMC9959191/ /pubmed/36838544 http://dx.doi.org/10.3390/molecules28041556 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Umino, Maho
Onozato, Mayu
Sakamoto, Tatsuya
Koishi, Mikoto
Fukushima, Takeshi
Analyzing Citramalic Acid Enantiomers in Apples and Commercial Fruit Juice by Liquid Chromatography–Tandem Mass Spectrometry with Pre-Column Derivatization
title Analyzing Citramalic Acid Enantiomers in Apples and Commercial Fruit Juice by Liquid Chromatography–Tandem Mass Spectrometry with Pre-Column Derivatization
title_full Analyzing Citramalic Acid Enantiomers in Apples and Commercial Fruit Juice by Liquid Chromatography–Tandem Mass Spectrometry with Pre-Column Derivatization
title_fullStr Analyzing Citramalic Acid Enantiomers in Apples and Commercial Fruit Juice by Liquid Chromatography–Tandem Mass Spectrometry with Pre-Column Derivatization
title_full_unstemmed Analyzing Citramalic Acid Enantiomers in Apples and Commercial Fruit Juice by Liquid Chromatography–Tandem Mass Spectrometry with Pre-Column Derivatization
title_short Analyzing Citramalic Acid Enantiomers in Apples and Commercial Fruit Juice by Liquid Chromatography–Tandem Mass Spectrometry with Pre-Column Derivatization
title_sort analyzing citramalic acid enantiomers in apples and commercial fruit juice by liquid chromatography–tandem mass spectrometry with pre-column derivatization
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9959191/
https://www.ncbi.nlm.nih.gov/pubmed/36838544
http://dx.doi.org/10.3390/molecules28041556
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