Column-switching high-performance liquid chromatography-fluorescence detection method for malic acid enantiomers in commercial wines

Onozato, Mayu; Kanda, Ryuji; Sato, Yushi; Sakamoto, Tatsuya; Umino, Maho; Fukushima, Takeshi

doi:10.1016/j.jfca.2021.104282

Cited by 8 publications

(7 citation statements)

References 21 publications

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“…S1 (G)). l -malic acid that is unstable and may form dimer is generally present in natural plants, however both d -malic acid and l -malic acid were recently found in fermented foods such as wines ( Onozato et al, 2022 ). According to computer-indicated retention time (RT) and corresponding peak area on each individual peak in HPLC chromatograms in the present study, the content of each individual organic acid can be easily calculated ( Table 1 ).…”

Section: Resultsmentioning

confidence: 99%

Culture condition optimization of naturally lacto-fermented cucumbers based on changes in detrimental and functional ingredients

Kao

Lin

2023

Food Chemistry: X

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Section: Resultsmentioning

confidence: 99%

Culture condition optimization of naturally lacto-fermented cucumbers based on changes in detrimental and functional ingredients

Kao

Lin

2023

Food Chemistry: X

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“…Meanwhile, only the S -form of Mal (i.e., l -Mal) has been reported to exist in fruits. Indeed, we observed only S -Mal in apples by column-switching HPLC using a fluorescence detection method [ 19 ]. Therefore, S -Mal is produced by fumarase (EC 4.2.1.2) in fruits via the Krebs cycle.…”

Section: Discussionmentioning

confidence: 99%

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

et al. 2023

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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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“…A cyclodextrin-based chiral stationary phase, Chiral CD-Ph, was utilized to separate the LA enantiomers derivatized with NBD-PZ, and the obtained Rs value was 1.98-4.57 [35]. Several polysaccharide-based columns were also employed for the chiral analysis of the hydroxy acids tagged with NBD-PZ [36][37][38]. A Chiralpak AD-RH column was utilized to separate the NBD-LA, 3HB or MA enantiomers.…”

Section: Enantioselective Separations Of La 2hb 3hb and Ma As Their N...mentioning

confidence: 99%

“…A Chiralpak AD-RH column was utilized to separate the NBD-LA, 3HB or MA enantiomers. The obtained Rs values of the NBD-LA and MA enantiomers were 1.83-3.86 [36,37] and 1.16 [38]; the separation of the NBD-3HB enantiomers was not completely achieved [37]. It was also reported that a Chiralpak AD-H column was used for the separations of the NBD-LA and 3HB enantiomers, and the hydroxy acid enantiomers were separated with Rs values of 7.06 and 4.27, respectively [37].…”

Section: Enantioselective Separations Of La 2hb 3hb and Ma As Their N...mentioning

confidence: 99%

“…Until now, to the best of our knowledge, no method has been developed to simultaneously analyze these hydroxy acid enantiomers in real biological samples by only one injection. However, the methods using an enzymatic reaction [19,20], capillary electrophoresis [21,22], gas chromatography [23,24], high-performance liquid chromatography (HPLC) with various detectors [25][26][27][28][29][30][31][32][33][34] and multi-dimensional HPLC methods [5,14,[35][36][37][38][39][40][41][42] have been reported to separately analyze these chiral hydroxy acids. Among them, HPLC methods (including column-switching/ multi-dimensional systems) are widely used for the chiral analysis of the hydroxy acids.…”

Section: Introductionmentioning

confidence: 99%

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Two-Dimensional Chiral HPLC Analysis of Lactate, Hydroxybutyrates and Malate in Human Plasma

et al. 2022

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For the simultaneous determination of lactate (LA), 2-hydroxybutyrate (2HB), 3-hydroxybutyrate (3HB) and malate (MA) enantiomers, a new separation technique in a two-dimensional high-performance liquid chromatography (2D-HPLC) system following the fluorescence derivatization with 4-nitro-7-piperazino-2,1,3-benzoxadiazole has been developed. The 2D-HPLC was composed of the reversed-phase (1D) and enantioselective (2D) separations. In the first dimension, the target hydroxy acids were separated as their D plus L mixtures on a Singularity RP18 column (1.0 mm i.d. x 250 mm), and the enantiomers were separated in the second dimension using a polysaccharide-based chiral stationary phase, Chiralpak IG (2.0 mm i.d. x 250 mm). By using the Chiralpak IG column, the LA, 2HB, 3HB and MA enantiomers were separated with resolution values of 3.47, 3.63, 6.81 and 3.72, respectively. The developed 2D-HPLC system was applied to human plasma, and trace levels of D-LA and L-3HB in addition to their major antipodes were determined. The acquired %D of LA (the percentage of D-LA over total LA) and %L of 3HB (the percentage of L-3HB over total 3HB) were 1.0 and 2.7, respectively. For 2HB, only the L-form was detected, while the MA enantiomers were not found in the human plasma.

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Column-switching high-performance liquid chromatography-fluorescence detection method for malic acid enantiomers in commercial wines

Cited by 8 publications

References 21 publications

Culture condition optimization of naturally lacto-fermented cucumbers based on changes in detrimental and functional ingredients

Culture condition optimization of naturally lacto-fermented cucumbers based on changes in detrimental and functional ingredients

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

Two-Dimensional Chiral HPLC Analysis of Lactate, Hydroxybutyrates and Malate in Human Plasma

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